Synthesis 2020; 52(22): 3295-3325
DOI: 10.1055/s-0040-1707884
review
© Georg Thieme Verlag Stuttgart · New York

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

,
School of Chemistry, Trinity College Dublin, The University of Dublin, Trinity Biomedical Sciences Institute, 152–160 Pearse Street, Dublin 2, Ireland   Email: sengem@tcd.ie
› Author Affiliations
This work was supported by a grant from Science Foundation Ireland (SFI IvP 13/IA/1894).
Further Information

Publication History

Received: 02 April 2020

Accepted after revision: 12 May 2020

Publication Date:
03 July 2020 (online)


Dedicated to Prof. Dr. Henning Hopf

Abstract

The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.

1 Introduction

2 Cubane

2.1 Cubane Synthesis

2.2 Cubane Functionalization

3 Bicyclo[1.1.1]pentane (BCP)

3.1 BCP Synthesis

3.2 BCP Functionalization

4 Adamantane

4.1 Adamantane Synthesis

4.2 Adamantane Functionalization

5 Conclusions and Outlook

 
  • References

  • 1 Hopf H. In Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives. Wiley-VCH; Weinheim: 2000
  • 2 Paquette LA. Proc. Natl. Acad. Sci. U.S.A. 1982; 79: 4495
  • 3 Eaton PE. Angew. Chem., Int. Ed. Engl. 1992; 31: 1421
    • 4a Paquette LA, Ternansky RJ, Balogh DW, Kentgen G. J. Am. Chem. Soc. 1983; 105: 5446
    • 4b Fessner W.-D, Murty BA. R. C, Prinzbach H. Angew. Chem., Int. Ed. Engl. 1987; 26: 451
    • 4c Fessner W.-D, Murty BA. R. C, Wörth J, Hunkler D, Fritz H, Prinzbach H, Roth WD, Schleyer P. vR, McEwen AB, Maier WF. Angew. Chem., Int. Ed. Engl. 1987; 26: 452
    • 4d Maier G, Pfriem S, Schäfer U, Matusch R. Angew. Chem., Int. Ed. Engl. 1978; 17: 520
    • 5a Locke GM, Bernhard SS. R, Senge MO. Chem. Eur. J. 2019; 25: 4590
    • 5b Kanazawa J, Uchiyama M. Synlett 2019; 30: 1
    • 5c Dilmaç AM, Spuling E, de Meijere A, Bräse S. Angew. Chem. Int. Ed. 2017; 56: 5684
    • 5d Biegasiewicz KF, Griffiths JR, Savage GP, Tsanaktsidis J, Priefer R. Chem. Rev. 2015; 115: 6719
    • 5e Levin MD, Kaszynski P, Michl J. Chem. Rev. 2000; 100: 169
    • 5f Wiberg KB. Chem. Rev. 1989; 89: 975
  • 6 Reaxys Database, https://www.reaxys.com (downloaded Feb 29, 2020).
    • 7a Davies WL, Grunert RR, Haff RF, McGahen JW, Neumayer EM, Paulshock M, Watts JC, Wood TR, Hermann EC, Hoffmann CE. Science 1964; 144: 862
    • 7b Tsunoda A, Maassab HF, Cochran KW, Eveland WC. Antimicrob. Agents Chemother. 1965; 553
    • 7c Fanta D. Wien. Med. Wochenschr. 1976; 126: 315
    • 7d Rosenthal KS, Sokol MS, Ingram RL, Subramanian R, Fort RC. Antimicrob. Agents Chemother. 1982; 22: 1031
    • 7e Savage SA, Jones GS, Kolotuchin S, Ramrattan SA, Vu T, Waltermire RE. Org. Process Res. Dev. 2009; 13: 1169
    • 7f Rosenstock J. Expert Rev. Endocrinol. Metabol. 2010; 5: 809
    • 7g Stockdale TP, Williams CM. Chem. Soc. Rev. 2015; 44: 7737
  • 8 Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
  • 9 Lovering F. MedChemComm 2013; 4: 515
  • 10 Aldeghi M, Malhotra S, Selwood DL, Chan AW. E. Chem. Biol. Drug Des. 2014; 83: 450
    • 11a Mykhailiuk PK. Org. Biomol. Chem. 2019; 17: 2839
    • 11b Ma X, Pham LN. Asian J. Org. Chem. 2020; 9: 8
  • 12 Pekker S, Kováts E, Oszlányi G, Bényei G, Klupp G, Bortel G, Ialsovszky I, Iakab E, Borondics F, Kamarás K, Bokor M, Kriza G, Tompa K, Faigel G. Nat. Mater. 2005; 4: 764
  • 13 Sakai N, Mareda J, Matile S. Acc. Chem. Res. 2005; 38: 79
  • 14 Zimmerman HE, McKelvey RD. J. Am. Chem. Soc. 1971; 93: 3638
    • 15a Locke GM, Senge MO. ECS Trans. 2016; 72: 1
    • 15b Metzger RM. J. Mater. Chem. 2008; 18: 4364
    • 16a Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
    • 16b Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
  • 17 He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
    • 18a Smith JM, Harwood SJ, Baran PS. Acc. Chem. Res. 2018; 51: 1807
    • 18b Murarka S. Adv. Synth. Catal. 2018; 360: 1735
    • 19a Hoffmann R, Hopf H. Angew. Chem. Int. Ed. 2008; 47: 4474
    • 19b Schleyer P. vR, Williams JE. J. Am. Chem. Soc. 1970; 92: 2377
  • 20 Weltner W. J. Am. Chem. Soc. 1953; 75: 4224
    • 21a Freedman HH. J. Am. Chem. Soc. 1961; 83: 2194
    • 21b Freedman HH, Petersen DR. J. Am. Chem. Soc. 1962; 84: 2837
  • 22 Throndsen HP, Zeiss H. J. Organomet. Chem. 1964; 1: 301
  • 23 Eaton PE, Cole TW. J. Am. Chem. Soc. 1964; 86: 962
  • 24 Chapman NB, Key JM, Toyne KJ. J. Org. Chem. 1970; 35: 3860
  • 25 Falkiner MJ, Littler SW, McRae KJ, Savage GP, Tsanaktsidis J. Org. Process Res. Dev. 2013; 17: 1503
  • 26 Eaton PE, Cole TW. J. Am. Chem. Soc. 1964; 86: 3157
  • 27 Gleiter R, Karcher M. Angew. Chem., Int. Ed. Engl. 1988; 27: 840
  • 28 Pelosi LF, Miller WT. J. Am. Chem. Soc. 1976; 98: 4311
  • 29 de Meijere A, Redlich S, Frank D, Magull J, Hofmeister A, Menzel H, Konig B, Svoboda J. Angew. Chem. Int. Ed. 2007; 46: 4574
  • 30 Chalmers BA, Xing H, Houston S, Clark C, Ghassabian S, Kuo A, Cao B, Reitsma A, Murray C.-EP, Stok JE, Boyle GM, Pierce CJ, Littler SW, Winkler DA, Bernhardt PV, Pasay C, DeVoss JJ, McCarthy J, Parsons PG, Walter GH, Smith MT, Cooper HM, Nilsson SK, Tsanaktsidis J, Savage GP, Williams CM. Angew. Chem. Int. Ed. 2016; 55: 3580
  • 31 Tristan AR, Williams CM, Rendina LM, Kassiou M. J. Med. Chem. 2019; 62: 1078
    • 32a Luh TY, Stock LM. J. Am. Chem. Soc. 1974; 96: 3712
    • 32b Srinivasan SK, Bläser D, Boese R, Desiraju GR. J. Org. Chem. 2001; 66: 1621
    • 32c Flanagan KJ, Bernhard SS. R, Plunkett S, Senge MO. Chem. Eur. J. 2019; 25: 6941
    • 32d Macreadie LK, Mensforth EJ, Babarao R, Konstas K, Telfer SG, Doherty CM, Tsanaktsidis J, Batten SR, Hill MR. J. Am. Chem. Soc. 2019; 141: 3828
    • 33a Eaton PE, Zhang MX, Gilardi R, Gelber N, Iyer S, Surapaneni R. Propellants, Explos., Pyrotech. 2002; 27: 1
    • 33b Zhang M.-X, Eaton PE, Gilardi R. Angew. Chem. Int. Ed. 2000; 39: 401
    • 33c Dallaston MA, Brusnahan JS, Wall C, Williams CM. Chem. Eur. J. 2019; 25: 8344
  • 34 Kybett BD, Carroll S, Natalis P, Bonnell DW, Margrave JL, Franklin JL. J. Am. Chem. Soc. 1966; 88: 626
  • 35 Sollott GP, Alster J, Gilbert EE, Sandus O, Slagg N. J. Energ. Mater. 1986; 4: 5
  • 36 Eaton PE, Ravi Shankar BK, Price GD, Pluth JJ, Gilbert EE, Alster J, Sandus O. J. Org. Chem. 1984; 49: 185
  • 37 Eaton PE, Wicks GE. J. Org. Chem. 1988; 53: 5353
  • 38 Lukin KA, Li J, Eaton PE, Kanomata N, Hain J, Punzalan E, Gilardi R. J. Am. Chem. Soc. 1997; 119: 9591
    • 39a Bashir-Hashemi A. Angew. Chem., Int. Ed. Engl. 1993; 32: 612
    • 39b Bashir-Hashemi A, Li J, Gelber N, Ammon H. J. Org. Chem. 1995; 60: 698
  • 40 Moriarty RM, Khosrowshahi JS, Dalecki TM. J. Chem. Soc., Chem. Commun. 1987; 675
    • 41a Barton DH. R, Lacher B, Zard SZ. Tetrahedron 1987; 43: 4321
    • 41b Barton DH. R, Crich D, Motherwell WB. Tetrahedron Lett. 1983; 24: 4979
  • 42 Tsanaktsidis J, Eaton PE. Tetrahedron Lett. 1989; 30: 6967
    • 43a Reddy DS, Sollott GP, Eaton PE. J. Org. Chem. 1989; 54: 722
    • 43b Irngartinger H, Strack S, Gredel F, Dreuw A, Della EW. Eur. J. Org. Chem. 1999; 1253
  • 44 Eaton PE, Maggini M. J. Am. Chem. Soc. 1988; 110: 7230
    • 45a Capriati V, Perna FM, Salomone A. Dalton Trans. 2014; 43: 14204
    • 45b Eaton PE, Tsanaktsidis J. J. Am. Chem. Soc. 1990; 112: 876
  • 46 Eaton PE, Pramod K, Emrick T, Gilardi R. J. Am. Chem. Soc. 1999; 121: 4111
    • 47a Eaton PE, Zhou JP. J. Am. Chem. Soc. 1992; 114: 3118
    • 47b Eaton PE, Yang CX, Xiong Y. J. Am. Chem. Soc. 1990; 112: 3225
  • 48 Kato Y, Williams CM, Uchiyama M, Matsubara S. Org. Lett. 2019; 21: 473
  • 49 Plunkett S, Flanagan KJ, Twamley B, Senge MO. Organometallics 2015; 34: 1408
    • 50a Schwab PF. H, Levin MD, Michl J. Chem. Rev. 1999; 99: 1863
    • 50b Schwab PF. H, Smith JR, Michl J. Chem. Rev. 2005; 105: 1197
  • 51 Negishi E, King AO, Klima WL, Patterson W, Silveira A. J. Org. Chem. 1980; 45: 2526
  • 52 Eaton PE, Stössel D. J. Org. Chem. 1991; 56: 5138
    • 53a Eaton PE, Galoppini E, Gilardi R. J. Am. Chem. Soc. 1994; 116: 7588
    • 53b Houston SD, Xing H, Bernhardt PV, Vanden Berg TJ, Tsanaktsidis J, Savage GP, Williams CM. Chem. Eur. J. 2019; 25: 2735
  • 54 Bernhard SS. R, Locke MG, Plunkett S, Meindl A, Flanagan KJ, Senge MO. Chem. Eur. J. 2018; 24: 1026
  • 55 Hoffmann R, Woodward RB. Acc. Chem. Res. 1968; 1: 17
    • 56a Eaton PE, Cassar L, Halpern J. J. Am. Chem. Soc. 1970; 92: 6366
    • 56b Moss S, King BT, de Meijere A, Kozhushkov SI, Eaton PE, Michl J. Org. Lett. 2001; 3: 2375
    • 56c Jalife S, Mondal S, Cabellos JL, Martinez-Guajardo G, Fernandez-Herrera MA, Merino G. Chem. Commun. 2016; 52: 3403
    • 57a Hassenrück K, Radziszewski JG, Balaji V, Murthy GS, McKinley AJ, David DE, Lynch VM, Martin H.-D, Michl J. J. Am. Chem. Soc. 1990; 112: 873
    • 57b Borden WT, Hrovat DA. J. Am. Chem. Soc. 1990; 112: 875
  • 58 Moriarty RM, Khosrowshahi JS, Miller RS, Flippen-Andersen J, Gilardi R. J. Am. Chem. Soc. 1989; 111: 8943
  • 59 Okada K, Okamoto K, Morita N, Okubo K, Oda M. J. Am. Chem. Soc. 1991; 113: 9401
  • 60 Toriyama F, Cornella J, Wimmer L, Chen T.-G, Dixon D, Creech G, Baran PS. J. Am. Chem. Soc. 2016; 138: 11132
  • 61 Fawcett A, Pradeilles J, Wang Y, Mutsuga T, Myers EL, Aggarwal VK. Science 2017; 357: 283
  • 62 Collin DE, Folgueiras-Amador AA, Pletcher D, Light ME, Linclau B, Brown RC. D. Chem. Eur. J. 2020; 26: 374
  • 63 Pellicciari R, Costantino G, Giovagnoni E, Mattoli L, Brabet I, Pin J.-P. Bioorg. Med. Chem. Lett. 1998; 8: 1569
    • 64a Curry K. WO 2004024709A2, 2004
    • 64b Houston SD, Chalmers BA, Savage GP, Williams CM. Org. Biomol. Chem. 2019; 17: 1067
    • 64c Wlochal J, Davies RD. M, Burton J. Org. Lett. 2014; 16: 4094
    • 64d Grover N, Locke GM, Flanagan KJ, Beh MH. R, Thompson A, Senge MO. Chem. Eur. J. 2020; 26: 2405
  • 65 Pati R, Karna SP. J. Chem. Phys. 2001; 115: 1703
  • 66 Lancaster JR, Martí AA, López-Gejo J, Jockusch S, O’Connor N, Turro NJ. Org. Lett. 2008; 10: 5509
  • 67 Wiberg KB. Tetrahedron Lett. 1985; 26: 599
  • 68 Wiberg KB, Connor DS, Lampmann GM. Tetrahedron Lett. 1964; 5: 531
  • 69 Wiberg KB, Connor DS. J. Am. Chem. Soc. 1966; 88: 4437
  • 70 Meinwald J, Szkrybalo W, Dimmel DR. Tetrahedron Lett. 1967; 8: 731
  • 71 Applequist DE, Wheeler JW. Tetrahedron Lett. 1977; 18: 3411
  • 72 Wiberg KB, Walker FH. J. Am. Chem. Soc. 1982; 104: 5239
    • 73a Semmler K, Szeimies G, Belzner J. J. Am. Chem. Soc. 1985; 107: 6410
    • 73b Lynch KM, Dailey WP. J. Org. Chem. 1995; 60: 4666
    • 73c Mondanaro KR, Dailey WP. Org. Synth. 1998; 75: 98
    • 74a Stohrer WD, Hoffmann R. J. Am. Chem. Soc. 1972; 94: 779
    • 74b Wiberg KB. J. Am. Chem. Soc. 1983; 105: 1227
    • 74c Chakrabarti P, Seiler P, Dunitz JD, Schlüter AD, Szeimies G. J. Am. Chem. Soc. 1981; 103: 7378
    • 74d Jackson JE, Allen LC. J. Am. Chem. Soc. 1984; 106: 59
    • 74e Werner M, Stephenson DS, Szeimies G. Liebigs Ann. Chem. 1996; 1705
    • 74f Wu W, Gu J, Song J, Shaik S, Hiberty PC. Angew. Chem. Int. Ed. 2009; 48: 1407
    • 75a Wiberg KB, Waddell ST. J. Am. Chem. Soc. 1990; 112: 2194

    • For a review, see:
    • 75b Delia EW, Lochert IJ. Org. Prep. Proced. Int. 1996; 28: 411
    • 76a Kaszynski P, McMurdie ND, Michl J. J. Org. Chem. 1991; 56: 307
    • 76b Wiberg KB, McMurdie N. J. Am. Chem. Soc. 1994; 116: 11990
  • 77 Hossain MT, Timberlake JW. J. Org. Chem. 2001; 66: 4409
  • 78 Wiberg KB, Waddell ST. Tetrahedron Lett. 1988; 29: 289
  • 79 Mazal C, Paraskos AJ, Michl J. J. Org. Chem. 1998; 63: 2116
    • 80a Messner M, Kozhushkov SI, de Meijere A. Eur. J. Org. Chem. 2000; 1137
    • 80b Kokhan SO, Valter YB, Tymtsunik AV, Komarov IV, Grygorenko OO. Eur. J. Org. Chem. 2017; 6450
    • 81a Caputo DF. J, Arroniz C, Dürr AB, Mousseau JJ, Stepan AF, Mansfield SJ, Anderson EA. Chem. Sci. 2018; 9: 5295
    • 81b Wong ML. J, Mousseau JJ, Mansfield SJ, Anderson EA. Org. Lett. 2019; 21: 2408; corrigendum: Org. Lett. 2019, 21, 4395
    • 81c Nugent J, Arroniz C, Shire BR, Sterling AJ, Pickford HD, Wong ML. J, Mansfield SJ, Caputo DF. J, Owen B, Mousseau JJ, Duarte F, Anderson EA. ACS Catal. 2019; 9: 9568
    • 82a Schwab PF. H, Noll BC, Michl J. J. Org. Chem. 2002; 67: 5476
    • 82b Kaleta J, Michl J, Mézière C, Simonov S, Zorina L, Wzietek P, Rodríguez-Fortea A, Canadell E, Batail P. CrystEngComm 2015; 17: 7829
    • 82c Kaleta J, Janoušek Z, Nečas M, Mazal C. Organometallics 2015; 34: 967
    • 83a Bunz U, Szeimies G. Tetrahedron Lett. 1989; 30: 2087
    • 83b Kaleta J, Mazal C. Org. Lett. 2011; 13: 1326
    • 83c Kaleta J, Marek N, Mazal C. Eur. J. Org. Chem. 2012; 4783
    • 83d Kaleta J, Bastien G, Císařová I, Batail P, Michl J. Eur. J. Org. Chem. 2018; 5137
  • 84 Kaleta J, Bastien G, Wen J, Dračínský M, Tortorici E, Císařová I, Beale PD, Rogers CT, Michl J. J. Org. Chem. 2019; 84: 8449
    • 85a Rodríguez-Fortea A, Kaleta J, Mézière C, Allain M, Canadell E, Wzietek P, Michl J, Batail P. ACS Omega 2018; 3: 1293
    • 85b Lemouchi C, Vogelsberg CS, Zorina L, Simonov S, Batail P, Brown S, Garcia-Garibay MA. J. Am. Chem. Soc. 2011; 133: 6371
    • 86a Rehm JD. D, Ziemer B, Szeimies G. Eur. J. Org. Chem. 1999; 2079
    • 86b Rehm JD. D, Ziemer B, Szeimies G. Eur. J. Org. Chem. 2001; 1049
    • 86c Makarov S, Brocklehurst CE, Karaghiosoff K, Koch G, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 12774
    • 86d Kondo M, Kanazawa J, Ichikawa T, Shimokawa T, Nagashima Y, Miyamoto K, Uchiyama M. Angew. Chem. Int. Ed. 2020; 59: 1970
    • 86e Yu S, Jing C, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2020; 59: 3917
    • 86f Garlets ZJ, Sanders JN, Malik H, Gampe C, Houk KN, Davies HM. L. Nat. Catal. 2020; 3: 351
    • 87a Lasányi D, Tolnai GL. Org. Lett. 2019; 21: 10057
    • 87b Yu S, Noble A, Bedford RB, Aggarwal VK. J. Am. Chem. Soc. 2019; 141: 20325
    • 88a Wiberg KB, Williams VZ. J. Org. Chem. 1970; 35: 369
    • 88b Della EW, Kasum B, Kirkbride KP. J. Am. Chem. Soc. 1987; 109: 2746
    • 88c Toops DS, Barbachyn MR. J. Org. Chem. 1993; 58: 6505
    • 88d Bunker KD, Sach NW, Huang Q, Richardson PF. Org. Lett. 2011; 13: 4746
    • 88e Thirumoorthi NT, Shen CJ, Adsool VA. Chem. Commun. 2015; 51: 3139
    • 88f Goh YL, Tam EK. W, Bernardo PH, Cheong CB, Johannes CW, William AD, Adsool VA. Org. Lett. 2014; 16: 1884
    • 89a Gianatassio R, Lopchuk JM, Wang J, Pan C.-M, Malins LR, Prieto L, Brandt TA, Collins MR, Gallego GM, Sach NW, Spangler JE, Zhu H, Zhu J, Baran PS. Science 2016; 351: 241
    • 89b Lopchuk JM, Fjelbye K, Kawamata Y, Malins LR, Pan C.-M, Gianatassio R, Wang J, Prieto L, Bradow J, Brandt TA, Collins MR, Elleraas J, Ewanicki J, Farrell W, Fadeyi OO, Gallego GM, Mousseau JJ, Oliver R, Sach NW, Smith JK, Spangler JE, Zhu H, Zhu J, Baran PS. J. Am. Chem. Soc. 2017; 139: 3209
    • 89c Kanazawa J, Maeda K, Uchiyama M. J. Am. Chem. Soc. 2017; 139: 17791
    • 89d Shelp RA, Walsh PJ. Angew. Chem. Int. Ed. 2018; 57: 15857
    • 89e Hughes JM. E, Scarlata DA, Chen AC.-Y, Burch JD, Gleason JL. Org. Lett. 2019; 21: 6800
    • 90a Ni S, Garrido-Castro AF, Merchant RR, de Gruyter JN, Schmitt DC, Mousseau JJ, Gallego GM, Yang S, Collins MR, Qiao JX, Yeung KS, Langley DR, Poss MA, Scola PM, Qin T, Baran PS. Angew. Chem. Int. Ed. 2018; 57: 14560
    • 90b Liang Y, Zhang X, MacMillan DW. C. Nature 2018; 559: 83
    • 90c VanHeyst MD, Qi J, Roecker AJ, Hughes JM. E, Cheng L, Zhao Z, Yin J. Org. Lett. 2020; 22: 1648
    • 90d Zhang X, Smith RT, Le C, McCarver SJ, Shireman BT, Carruthers NI, MacMillan DW. C. Nature 2020; 580: 220
    • 90e Kim JH, Ruffoni A, Al-Faiyz YS. S, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2020; 59: 8225
    • 91a Bär RM, Kirschner S, Nieger M, Bräse S. Chem. Eur. J. 2018; 24: 1373
    • 91b Bär RM, Heinrich G, Nieger M, Fuhr O, Bräse S. Beilstein J. Org. Chem. 2019; 15: 1172
    • 91c Bär RM, Langer L, Nieger M, Bräse S. Adv. Synth. Catal. 2020; 362: 1356
    • 92a Corey EJ, Seebach D. Angew. Chem., Int. Ed. Engl. 1965; 4: 1077
    • 92b Trongsiriwat N, Pu Y, Nieves-Quinones Y, Shelp RA, Kozlowski MC, Walsh PJ. Angew. Chem. Int. Ed. 2019; 58: 13416
    • 92c Rout SK, Marghem G, Lan J, Leyssens T, Riant O. Chem. Commun. 2019; 55: 14976
  • 93 de Meijere A, Zhao L, Belov VN, Bossi M, Noltemeyer M, Hell SW. Chem. Eur. J. 2007; 13: 2503
    • 94a Levin MD, Hamrock SJ, Kaszynski P, Shtarev AB, Levina GA, Noll BC, Ashley ME, Newmark R, Moore GG. I, Michl J. J. Am. Chem. Soc. 1997; 119: 12750
    • 94b Shtarev AB, Pinkhassik E, Levin MD, Stibor I, Michl J. J. Am. Chem. Soc. 2001; 123: 3484
    • 94c Kaleta J, Rončević I, Císařová I, Dračínský M, Šolínová V, Kašička V, Michl J. J. Org. Chem. 2019; 84: 2448
    • 95a Measom ND, Down KD, Hirst DJ, Jamieson C, Manas ES, Patel VK, Somers DO. ACS Med. Chem. Lett. 2017; 8: 43
    • 95b Ma X, Sloman DL, Han Y, Bennett DJ. Org. Lett. 2019; 21: 7199
    • 95c Bychek RM, Hutskalova V, Bas YP, Zaporozhets OA, Zozulya S, Levterov VV, Mykhailiuk PK. J. Org. Chem. 2019; 84: 15106
  • 96 Wanka L, Iqbal K, Schreiner PR. Chem. Rev. 2013; 113: 3516
    • 97a Landa S, Macháček V. Collect. Czech. Chem. Commun. 1933; 5: 1
    • 97b Rollmann LD, Green LA, Bradway RA, Timken HK. C. Catal. Today 1996; 31: 163
    • 98a Schleyer P. vR. J. Am. Chem. Soc. 1957; 79: 3292
    • 98b Fort RC, Schleyer P. vR. Chem. Rev. 1964; 64: 277
    • 99a Nekrasova VA, Shuikin II. Russ. Chem. Bull. 1969; 18: 649
    • 99b Olah GA, Lin HC. H. J. Am. Chem. Soc. 1971; 93: 1259
    • 99c Akhrem IS, Avetisyan DV, Afanas’eva LV, Goryunov EI, Churilova IM, Petrovskii PV, Kagramanov ND. Mendeleev Commun. 2011; 21: 259
    • 99d Reichert VR, Mathias LJ. Macromolecules 1994; 27: 7015
    • 100a Webber WC, Harthoorn PA. GB 819240, 1959
    • 100b Zapf A, Ehrentraut A, Beller M. Angew. Chem. Int. Ed. 2000; 39: 4153
    • 100c Agnew-Francisa KA, Williams CM. Adv. Synth. Catal. 2016; 358: 675
    • 101a Egloff G, Schaad RE, Lowry CD. Chem. Rev. 1931; 8: 1
    • 101b Zhao M, Lu W. Org. Lett. 2018; 20: 5264
    • 102a Smith GW, Williams HD. J. Org. Chem. 1961; 26: 2207
    • 102b Baughman GL. J. Org. Chem. 1964; 29: 238
    • 103a Stetter H, Schwarz M, Hirschhorn A. Angew. Chem. 1959; 71: 429
    • 103b Sasaki T, Eguchi S, Toru T. Bull. Korean Chem. Soc. 1968; 41: 236
  • 104 Ohno M, Ishizaki K, Eguchi S. J. Org. Chem. 1988; 53: 1285
  • 105 Bräse S, Waegell B, de Meijere A. Synthesis 1998; 148
  • 106 Someya H, Yorimitsu H, Oshima K. Tetrahedron Lett. 2009; 50: 3270
  • 107 Ghorai SK, Jin M, Hatakeyama T, Nakamura M. Org. Lett. 2012; 14: 1066
    • 108a Zultanski SL, Fu GC. J. Am. Chem. Soc. 2013; 135: 624
    • 108b Pouwer RH, Williams CM, Raine AL, Harper JB. Org. Lett. 2005; 7: 1323
    • 108c Pouwer RH, Harper JB, Vyakaranam K, Michl J, Williams CM, Jessen CH, Bernhardt PV. Eur. J. Org. Chem. 2007; 241
  • 109 Molle G, Bauer P, Dubois JE. J. Org. Chem. 1982; 47: 4120
  • 110 Rieke RD, Hanson MV, Brown JD. J. Org. Chem. 1996; 61: 2726
  • 111 Lohre C, Dröge T, Wang C, Glorius F. Chem. Eur. J. 2011; 17: 6052
    • 112a Sämann C, Dhayalan V, Schreiner PR, Knochel P. Org. Lett. 2014; 16: 2418
    • 112b Milne JE, Buchwald SL. J. Am. Chem. Soc. 2004; 126: 13028
    • 113a Recupero F, Bravo A, Bjørsvik H.-R, Fontana F, Minisci F, Piredda M. J. Chem. Soc., Perkin Trans. 2 1997; 2399
    • 113b Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70
  • 114 Berndt J.-P, Erb F, Ochmann L, Beppler J, Schreiner P. Synlett 2019; 30: 493
  • 115 Yang H.-B, Feceu A, Martin DB. C. ACS Catal. 2019; 9: 5708
    • 116a Tominaga M, Kunitomi N, Katagiri K, Itoh T. Org. Lett. 2015; 17: 786
    • 116b Tominaga M, Takahashi E, Ukai H, Ohara K, Itoh T, Yamaguchi K. Org. Lett. 2017; 19: 1508
    • 116c Tominaga M, Takahashi E, Ukai H, Ohara K, Itoh T, Yamaguchi K. J. Org. Chem. 2019; 84: 5109
  • 117 Kahl P, Wagner JP, Balestrieri C, Becker J, Hausmann H, Bodwell GJ, Schreiner PR. Angew. Chem. Int. Ed. 2016; 55: 9277
  • 118 Basel BS, Zirzlmeier J, Hetzer C, Phelan BT, Krzyaniak MD, Reddy SR, Coto PB, Horwitz NE, Young RM, White FJ, Hampel F, Clark T, Thoss M, Tykwinski RR, Wasielewski MR, Guldi DM. Nat. Commun. 2017; 8: 15171
    • 119a Pathak R, Marx A. Chem. Asian J. 2011; 6: 1450
    • 119b Štimac A, Šekutor M, Mlinarić-Majerski K, Frkanec L, Frkanec R. Molecules 2017; 22: 297
    • 120a Newman H. Synthesis 1972; 692
    • 120b Pannier N, Maison W. Eur. J. Org. Chem. 2008; 1278
    • 121a Radhakrishnan U, Schweiger M, Stang PJ. Org. Lett. 2001; 3: 3141
    • 121b Trawny D, Kunz V, Reissig H.-U. Eur. J. Org. Chem. 2014; 6295
  • 122 Tominaga M, Ohara K, Yamaguchi K, Azumaya I. J. Org. Chem. 2014; 79: 6738
    • 123a Grigg R, Elboray EE, Aly MF, Abbas-Temirek HH. Chem. Commun. 2012; 48: 11504
    • 123b Kitagawa T, Matsubara H, Komatsu K, Hirai K, Okazaki T, Hase T. Langmuir 2013; 29: 4275
    • 123c Franzmann E, Khalil F, Weidmann C, Schröder M, Rohnke M, Janek J, Smarsly BM, Maison W. Chem. Eur. J. 2011; 17: 8596
    • 123d Senchyk GA, Lysenko AB, Boldog I, Rusanov EB, Chernega AN, Krautscheidc H, Domasevitch KV. Dalton Trans. 2012; 41: 8675
  • 124 Lee GS, Bashara JN, Sabih G, Oganesyan A, Godjoian G, Duong HM, Marinez ER, Gutiérrez CG. Org. Lett. 2004; 6: 1705
    • 125a Sollott GP, Gilbert EE. J. Org. Chem. 1980; 45: 5405
    • 125b Ermer O. J. Am. Chem. Soc. 1988; 110: 3747
    • 125c Bashir-Hashemi A, Li J, Gelber N. Tetrahedron Lett. 1995; 36: 1233
  • 126 Mathias LJ, Reichert VR, Muir AV. G. Chem. Mater. 1993; 5: 4
    • 127a Schilling CI, Plietzsch O, Nieger M, Muller T, Bräse S. Eur. J. Org. Chem. 2011; 1743
    • 127b Schilling CI, Bräse S. Org. Biomol. Chem. 2007; 5: 3586
    • 127c Plietzsch O, Schilling CI, Tolev M, Nieger M, Richert C, Muller T, Bräse S. Org. Biomol. Chem. 2009; 7: 4734
  • 128 Dufrêne YF, Ando T, Garcia R, Alsteens D, Martinez-Martin D, Engel A, Gerber C, Müller DJ. Nat. Nanotechnol. 2017; 12: 295
  • 129 Li Q, Rukavishnikov AV, Petukhov PA, Zaikova TO, Jin C, Keana JF. W. J. Org. Chem. 2003; 68: 4862
  • 130 Martin VV, Alferiev IS, Weis AL. Tetrahedron Lett. 1999; 40: 223
  • 131 Hetzer C, Basel BS, Kopp SM, Hampel F, White FJ, Clark T, Guldi DM, Tykwinski RR. Angew. Chem. Int. Ed. 2019; 58: 15263
    • 132a Humblet V, Misra P, Bhushan KR, Nasr K, Ko YS, Tsukamoto T, Pannier N, Frangioni JV, Maison W. J. Med. Chem. 2009; 52: 544
    • 132b Pavet V, Beyrath J, Pardin C, Morizot A, Lechner MC, Briand JP, Wendland M, Maison W, Fournel S, Micheau O, Guichard G, Gronemeyer H. Cancer Res. 2010; 70: 1101
    • 132c Maison W, Frangioni JV, Pannier N. Org. Lett. 2004; 6: 4567
    • 133a Fleck C, Franzmann E, Claes D, Rickert A, Maison W. Synthesis 2013; 45: 1452
    • 133b Lamanna G, Russier J, Ménard-Moyon C, Bianco A. Chem. Commun. 2011; 47: 8955