Macrocyclic Hosts in Asymmetric Phase-Transfer Catalyzed Reactions

Rosaria Schettini; Marina Sicignano; Francesco De Riccardis; Irene Izzo; Giorgio Della Sala

doi:10.1055/s-0037-1610311

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(24): 4777-4795
DOI: 10.1055/s-0037-1610311

short review

Macrocyclic Hosts in Asymmetric Phase-Transfer Catalyzed Reactions

Authors

Rosaria Schettini
Marina Sicignano
Francesco De Riccardis
Irene Izzo
Giorgio Della Sala *

Dipartimento di Chimica e Biologia ‘A. Zambelli’, Università degli Studi di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano (SA), Italy eMail: gdsala@unisa.it

Abstract

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Abstract

The introduction and development of neutral macrocyclic hosts capable of complexing ions within their pre-organized cavity, has been of utmost importance in supramolecular chemistry. Their ability to form stable organic-soluble metal–macrocycle complexes opened up the way to their application in phase-transfer catalysis (PTC) as a viable alternative to quaternary onium salts. In particular, their conformationally rigid preorganized backbone, accommodating organic substrates in defined orientations, promotes highly efficient stereoselective reactions. This short review summarizes the applications of neutral macrocyclic hosts in stereoselective PTC, highlighting the difference and possible complementarity with quaternary ammonium salts.

1 Introduction

2 Crown Ethers and Related Coronands

2.1 Enantioselective PTC with Chiral Macrocyclic Coronands

2.2 Enantioselective PTC Reactions Catalyzed by Chiral Quaternary Ammonium Salts with Achiral Crown Ether Co-catalysts

3 Cyclic Peptoids

4 Miscellaneous Chiral Macrocyclic Hosts

5 Summary and Outlook

Key words

asymmetric catalysis - crown compounds - host-guest systems - macrocycles - phase-transfer catalysis - calixarenes - cyclic peptoids

Volltext

Referenzen

References

1a Starks CM. Liotta CL. Halpern ME. Phase-Transfer Catalysis, Fundamentals, Applications, and Industrial Perspectives. Chapman & Hall; New York: 1994
1b Phase-Transfer Catalysis, Fundamentals, Mechanisms and Syntheses. Halpern ME. American Chemical Society; Washington, DC: 1997
1c Starks CM. Liotta CL. Phase-Transfer Catalysis, Principles and Techniques. Academic Press; New York: 1978
1d Handbook of Phase-Transfer Catalysis. Sasson Y. Neumann R. Chapman & Hall; London: 1997
1e Albanese D. Catal. Rev.: Sci. Eng. 2003; 45: 369
1f Naik SD. Doraiswamy LK. AIChE J. 1998; 44: 612

2a Ikunaka M. Org. Process Res. Dev. 2008; 12: 698
2b Freedman HH. Pure Appl. Chem. 1986; 58: 857
2c Sharma M. In Handbook of Phase-Transfer Catalysis. Sasson Y. Neumann R. Chapman Hall; London: 1997: 168
2d Fedoryński M. Jezierska-Zięba M. Kąkol B. Acta Pol. Pharm. 2008; 65: 647
2e Tan J. Yasuda N. Org. Process Res. Dev. 2015; 19: 1731

3a Mąkosza M. In Handbook of Phase-Transfer Catalysis. Sasson Y. Neumann R. Chapman Hall; London: 1997: 135
3b Mąkosza M. In Phase-Transfer Catalysis, Fundamentals, Mechanisms and Syntheses. Halpern ME. American Chemical Society; Washington, DC: 1997: 41
3c Mąkosza M. Pure Appl. Chem. 2000; 72: 1399

4 Mąkosza M. Pure Appl. Chem. 1975; 43: 439

5a Asymmetric Phase Transfer Catalysis. Maruoka K. Wiley-VCH; Weinheim: 2008
5b Shirakawa S. Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312
5c Ooi T. Maruoka K. Angew. Chem. Int. Ed. 2007; 46: 4222
5d Kaneko S. Kumatabara Y. Shirakawa S. Org. Biomol. Chem. 2016; 14: 5367
5e Jew S.-s. Park H.-g. Chem. Commun. 2009; 7090
5f Albanese DC. M. Foschi F. Penso M. Org. Process Res. Dev. 2016; 20: 129
5g Hashimoto T. Maruoka K. Chem. Rev. 2007; 107: 5656

For selected examples:

6a He R. Wang X. Hashimoto T. Maruoka K. Angew. Chem. Int. Ed. 2008; 47: 9466
6b Zhu C.-L. Zhang F.-G. Meng W. Nie J. Cahard D. Ma J.-A. Angew. Chem. Int. Ed. 2011; 50: 5869
6c Shirakawa S. Kasai A. Tokuda T. Maruoka K. Chem. Sci. 2013; 4: 2248
6d Shirakawa S. Tokuda T. Kasai A. Maruoka K. Org. Lett. 2013; 15: 3350
6e Shirakawa S. Koga K. Tokuda T. Yamamoto K. Maruoka K. Angew. Chem. Int. Ed. 2014; 53: 6220
6f Cao D. Chai Z. Zhang J. Ye Z. Xiao H. Wang H. Chen J. Wu X. Zhao G. Chem. Commun. 2013; 49: 5972

For selected examples:

7a Ohmatsu K. Kiyokawa M. Ooi T. J. Am. Chem. Soc. 2011; 133: 1307
7b Uraguchi D. Sasaki S. Ooi T. J. Am. Chem. Soc. 2007; 129: 12392
7c Wang C. Zong L. Tan C.-H. J. Am. Chem. Soc. 2015; 137: 10677
7d Kita T. Georgieva A. Hashimoto Y. Nakata T. Nagasawa K. Angew. Chem. Int. Ed. 2002; 41: 2832
7e Howard-Jones A. Caulkett PW. R. Murphy PJ. Thomas D. J. Org. Chem. 1999; 64: 1039
7f Belokon YN. I. Maleev V. North M. Larionov VA. Savel’yeva TF. Nijland A. Nelyubina YV. ACS Catal. 2013; 3: 1951

8a Liotta CL. Harris HP. J. Am. Chem. Soc. 1974; 96: 2250
8b Pedersen CJ. Frensdorff HK. Angew. Chem., Int. Ed. Engl. 1972; 11: 16

9a Xia L. Jia Y. Tong S. Wang J. Han G. Kinet. Catal. 2010; 51: 69
9b Shirakawa S. Yamamoto K. Kitamura M. Ooi T. Maruoka K. Angew. Chem. Int. Ed. 2005; 44: 625

10 Landini D. Maia A. Montanari F. Pirisi F. J. Chem. Soc., Perkin Trans. 2 1980; 46
11 Gobbi A. Landini D. Maia A. Petricci S. J. Org. Chem. 1998; 63: 5356

12a Liotta CL. Berkner J. Wright J. Fair B. In Phase-Transfer Catalysis, Fundamentals, Mechanisms and Syntheses. Halpern ME. American Chemical Society; Washington, DC: 1997: 29
12b Pliego JR. Jr. Riveros JM. J. Mol. Catal. A: Chem. 2012; 363–364: 489

13a Esikova IA. In Handbook of Phase-Transfer Catalysis. Sasson Y. Neumann R. Chapman & Hall; London: 1997: 1
13b Albanese D. Landini D. Maia M. Penso M. Ind. Eng. Chem. Res. 2001; 2396
13c Starks CM. Owens RM. J. Am. Chem. Soc. 1973; 95: 3613
13d Dermeik S. Sasson Y. J. Org. Chem. 1985; 50: 879
13e Zahalka HA. Sasson Y. J. Chem. Soc., Chem. Commun. 1984; 1652
13f Yee HA. Palmer HJ. Chen SH. Chem. Eng. Prog. 1987; 83: 33
13g Czech BP. Pugia MJ. Bartsch R. Tetrahedron 1985; 41: 5439
13h Dehmlow EV. Raths HC. J. Chem. Res., Synop. 1988; 384

14a Dehmlow EV. In Phase-Transfer Catalysis, Fundamentals, Mechanisms and Syntheses. Halpern ME. American Chemical Society; Washington, DC: 1997: 108 ; and references cited therein
14b Reinholz E. Becker A. Hagenbruch B. Schäfer S. Schmitt A. Synthesis 1990; 1069
14c Della Sala G. Sicignano M. Schettini R. De Riccardis F. Cavallo L. Minenkov Y. Batisse C. Hanquet G. Leroux F. Izzo I. J. Org. Chem. 2017; 82: 6629

15 Maia A. Landini D. Petricci S. Supramol. Chem. 2000; 12: 203

16a Weber E. Vögtle F. In Host Guest Complex Chemistry – Macrocycles – Synthesis, Structures, Applications. Weber E. Vögtle F. Springer; Berlin: 1985: 1
16b Smid J. Angew. Chem., Int. Ed. Engl. 1972; 11: 112

17 Landini D. Maia A. Montanari F. J. Am. Chem. Soc. 1984; 106: 2917

18a Comprehensive Supramolecular Chemistry II. Gokel GW. Atwood JL. Elsevier; Amsterdam: 2017. 2nd ed., Vol. 1
18b Comprehensive Supramolecular Chemistry II. Rissanen K. Elsevier; Amsterdam: 2017. 2nd ed., Vol. 3
18c Macrocyclic Chemistry: Current Trends and Future Perspectives. Gloe K. Springer; Dordrecht: 2005
18d Gokel GW. Leevy WM. Weber ME. Chem. Rev. 2004; 104: 2723
18e Liu Z. Nalluri SK. M. Stoddart JF. Chem. Soc. Rev. 2017; 46: 2459
18f Reinhoudt DN. van Veggel FC. J. M. Pure Appl. Chem. 1993; 65: 965
18g Izatt RM. Pawlak K. Bradshaw JS. Chem. Rev. 1995; 95: 2529

19a Vaquero M. Rovira L. Vidal-Ferran A. Chem. Commun. 2016; 52: 11038
19b Supramolecular Catalysis. van Leeuwen PW. N. M. Wiley-VCH; Weinheim: 2008
19c Sasaki S. Koga K. In Crown Ethers and Analogous Compounds. Hiraoka M. Elsevier; Amsterdam: 1992: 265
19d Kellogg RM. Angew. Chem., Int. Ed. Engl. 1984; 23: 782
19e Dong Z. Luo Q. Liu J. Chem. Soc. Rev. 2012; 41: 7890

20 Cram DJ. Sogah GD. Y. J. Chem. Soc., Chem. Commun. 1981; 625
21 Sutherland IO. J. Chem. Soc., Faraday Trans. 1986; 82: 1145

22a Tarí S. Chinchilla R. Nájera C. Tetrahedron: Asymmetry 2010; 21: 2872
22b Park EJ. Kim MH. Kim DY. J. Org. Chem. 2004; 69: 6897
22c Alvarez R. Hourdin M.-A. Cavé C. d’Angelo J. Chaminade P. Tetrahedron Lett. 1999; 40: 7091

23 Cram DJ. Sogah GD. Y. J. Am. Chem. Soc. 1985; 107: 8301
24 Takasu M. Wakabayashi H. Furuta K. Yamamoto H. Tetrahedron Lett. 1988; 29: 6943
25 Aoki S. Sasaki S. Koga K. Tetrahedron Lett. 1989; 30: 7229
26 Dehmlow EV. Knufinke V. Liebigs Ann. Chem. 1992; 283
27 Crosby J. Stoddart JF. Sun X. Venner MR. W. Synthesis 1993; 141
28 Brunet E. Poveda AM. Rabasco D. Oreja E. Font LM. Batra MS. Rodríguez-Ubis JC. Tetrahedron: Asymmetry 1994; 5: 935
29 Nair V. Prabhakarana J. Eigendod GK. Synth. Commun. 1997; 27: 3095
30 Xie J. Bogliotti N. Chem. Rev. 2014; 114: 7678

31a Alonso-López M. Martín-Lomas M. Penadés S. Tetrahedron Lett. 1986; 27: 3551
31b Jimenez-Barbero J. Martín-Lomas M. Penadés S. Tetrahedron 1988; 44: 1535

32 van Maarschalkerwaart DA. H. Willard NP. Pandit UK. Tetrahedron 1992; 48: 8825
33 Kanakamma PP. Mani NS. Maitra U. Nair V. J. Chem. Soc., Perkin Trans. 1 1995; 2339
34 Dondoni A. Marra A. Tetrahedron Lett. 2009; 50: 3593

35a Tőke L. Bakó P. Keserű GM. Albert M. Fenichel L. Tetrahedron 1998; 54: 213
35b Tőke L. Fenichel L. Albert M. Tetrahedron Lett. 1995; 36: 5951

36 A similar enantioselectivity in the addition of 10 to 8 catalyzed by a chiral tripodal oxazoline host (82% ee) has been reported: Kim S.-G. Ahn KH. Tetrahedron Lett. 2001; 42: 4175

For selected examples of highly enantioselective alkylation with alkyl halides see:

37a Ooi T. Kameda M. Maruoka K. J. Am. Chem. Soc. 1999; 121: 6519
37b Kitamura M. Shirakawa S. Maruoka K. Angew. Chem. Int. Ed. 2005; 44: 1549
37c Han Z. Yamaguchi Y. Kitamura M. Maruoka K. Tetrahedron Lett. 2005; 46: 8555
37d Lygo B. Allbutt B. James SR. Tetrahedron Lett. 2003; 44: 5629
37e Jew S.-S. Yoo M.-S. Jeong B.-S. Park IY. Park H.-G. Org. Lett. 2002; 4: 4245
37f Yoo M.-S. Jeong B.-S. Lee JH. Park H.-G. Jew S.-S. Org. Lett. 2005; 7: 1129

For examples of highly enantioselective Michael addition with vinyl acceptors, see:

38a Lygo B. Beynon C. Lumley C. McLeod MC. Wade CE. Tetrahedron Lett. 2009; 50: 3363
38b Lygo B. Allbutt B. Kirton EH. M. Tetrahedron Lett. 2005; 46: 4461
38c Wang Y.-G. Kumano T. Kano T. Maruoka K. Org. Lett. 2009; 11: 2027
38d Corey EJ. Noe MC. Xu F. Tetrahedron Lett. 1998; 39: 5347
38e Bernardi L. López-Cantarero J. Niess B. Jørgensen KA. J. Am. Chem. Soc. 2007; 129: 5772
38f Ma T. Fu X. Kee CW. Zong L. Pan Y. Huang K.-W. Tan C.-H. J. Am. Chem. Soc. 2011; 133: 2828
38g Sheshenev AE. Boltukhina EV. White AJ. P. Hii KK. Angew. Chem. Int. Ed. 2013; 52: 6988

39 Itoh T. Shirakami S. Heterocycles 2001; 55: 37
40 Yonezawa K. Patil ML. Sasai H. Takizawa S. Heterocycles 2005; 66: 639
41 Akiyama T. Hara M. Fuchibe K. Sakamoto S. Yamaguchi K. Chem. Commun. 2003; 1734

For more enantioselective additions of N-(diphenylmethylene)glycine esters to acrylonitrile under PTC conditions, see:

42a Zhang F.-Y. Corey EJ. Org. Lett. 2000; 2: 1097
42b ref. 38b
42c Chinchilla R. Mazón P. Nájera C. Ortega FJ. Yus M. ARKIVOC 2005; vi: 222 ; http://www.arkat-usa.org/home
42d Maleev VI. North M. Larionov VA. Fedyanin IV. Savel’yeva TF. Moscalenko MA. Smolyakov AF. Belokon YN. Adv. Synth. Catal. 2014; 356: 1803

43 Pham TS. Czirok JB. Balázs L. Pál K. Kubinyi M. Bitter I. Jászay Z. Tetrahedron: Asymmetry 2011; 22: 480

44a Jászay Z. Pham TS. Németh G. Bakó P. Petneházy I. Tőke L. Synlett 2009; 1429
44b Pham TS. Rapi Z. Bakó P. Petneházy I. Stirling A. Jászay Z. New J. Chem. 2017; 41: 14945

45 Jászay Z. Tódor I. Rapi Z. Bakó P. Petneházy I. Tőke L. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 659
46 de Vries EF. J. Ploeg L. Colao M. Brussee J. van der Gen A. Tetrahedron: Asymmetry 1995; 6: 1123

47a Masui M. Ando A. Shioiri T. Tetrahedron Lett. 1988; 29: 2835
47b Dehmlow EV. Düttmann S. Neumann B. Stammler H.-G. Eur. J. Org. Chem. 2002; 2087

48 Sim S.-BD. Wang M. Zhao Y. ACS Catal. 2015; 5: 3609
49 Stoddart JF. Biochem. Soc. Trans. 1987; 15: 1188
50 Dehmlow EV. Sauerbier C. Liebigs Ann. Chem. 1989; 181
51 Aoki S. Sasaki S. Koga K. Heterocycles 1992; 33: 493
52 Bakó P. Szöllősy Á. Bombicz P. Tőke L. Synlett 1997; 291

53a Bakó P. Kiss T. Tőke L. Tetrahedron Lett. 1997; 38: 7259
53b Bakó P. Bajor Z. Tőke L. J. Chem. Soc., Perkin Trans. 1 1999; 3651

54a Bakó P. Vizvárdi K. Toppet S. Van der Eycken E. Hoornaert GJ. Tőke L. Tetrahedron 1998; 54: 14975
54b Bakó P. Vizvárdi K. Bajor Z. Tőke L. Chem. Commun. 1998; 1193

55 Bakó P. Czinege E. Bakó T. Czugler M. Tőke L. Tetrahedron: Asymmetry 1999; 10: 4539
56 Bakó P. Keglevich G. Rapi Z. Lett. Org. Chem. 2010; 7: 645
57 Novák T. Tatai J. Bakó P. Czugler M. Keglevich G. Tőke L. Synlett 2001; 424
58 Bakó P. Makó A. Keglevich G. Kubinyi M. Pál K. Tetrahedron: Asymmetry 2005; 16: 1861
59 Makó A. Szöllősy Á. Keglevich G. Menyhárd DK. Bakó P. Tőke L. Monatsh Chem. 2008; 139: 525
60 Bakó P. Tőke L. Szöllősy Á. Bombicz P. Heteroat. Chem. 1997; 8: 333
61 Novák T. Bakó P. Keglevich G. Greiner I. Phosphorus, Sulfur Silicon Relat. Elem. 2007; 182: 2449
62 Rapi Z. Nemcsok T. Pálvölgyi Á. Keglevich G. Grün A. Bakó P. Chirality 2017; 29: 257
63 Szabó T. Rapi Z. Keglevich G. Szöllősy Á. Drahos L. Bakó P. ARKIVOC 2012; viii: 36 ; http://www.arkat-usa.org/home
64 Bakó P. Bakó T. Bisztray K. Szöllősy Á. Nagy K. Tőke L. J. Incl. Phenom. Macrocycl. Chem. 2001; 39: 247
65 Bakó T. Bakó P. Keglevich G. Báthori N. Czugler M. Tatai J. Novák T. Parlagh G. Tőke L. Tetrahedron: Asymmetry 2003; 14: 1917
66 Makó A. Rapi Z. Drahos L. Szöllősy Á. Keglevich G. Bakó P. Lett. Org. Chem. 2010; 7: 424
67 Bakó T. Bakó P. Szöllősy Á. Czugler M. Keglevich G. Tőke L. Tetrahedron: Asymmetry 2002; 13: 203
68 Makó A. Rapi Z. Keglevich G. Szöllősy Á. Drahos L. Hegedűs L. Bakó P. Tetrahedron: Asymmetry 2010; 21: 919

69a Bakó T. Bakó P. Keglevich G. Bombicz P. Kubinyi M. Pál K. Bodor S. Makó A. Tőke L. Tetrahedron: Asymmetry 2004; 15: 1589
69b Bakó P. Bakó T. Mészáros A. Keglevich G. Szöllősy Á. Bodor S. Makó A. Tőke L. Synlett 2004; 643
69c Rapi Z. Szabó T. Keglevich G. Szöllősy Á. Drahos L. Bakó P. Tetrahedron: Asymmetry 2011; 22: 1189

70 Makó A. Menyhárd DK. Bakó P. Keglevich G. Tőke L. J. Mol. Struct. 2008; 892: 336

For selected examples, see:

71a Corey EJ. Zhang F.-Y. Org. Lett. 1999; 1: 1287
71b Ooi T. Ohara D. Tamura M. Maruoka K. J. Am. Chem. Soc. 2004; 126: 6844
71c Yoo M.-S. Kim D.-G. Ha MW. Jew S.-s. Park H.-g. Jeong B.-S. Tetrahedron Lett. 2010; 51: 5601
71d Jew S.-s. Lee J.-H. Jeong B.-S. Yoo M.-S. Kim M.-J. Lee Y.-J. Lee J. Choi S.-h. Lee K. Lah MS. Park H.-g. Angew. Chem. Int. Ed. 2005; 44: 1383
71e Lygo B. Gardiner SD. McLeod MC. To DC. M. Org. Biomol. Chem. 2007; 5: 2283
71f Lygo B. Wainwright PG. Tetrahedron 1999; 55: 6289

72 Adam W. Rao PB. Degen H.-G. Saha-Möller CR. Tetrahedron: Asymmetry 2001; 12: 121
73 Rapi Z. Bakó P. Keglevich G. Szöllősy Á. Drahos L. Botyánszki A. Holczbauer T. Tetrahedron: Asymmetry 2012; 23: 489
74 Arai S. Shirai Y. Ishida T. Shioiri T. Tetrahedron 1999; 55: 6375
75 Liu Y. Provencher BA. Bartelson KJ. Deng L. Chem. Sci. 2011; 2: 1301

76a Rapi Z. Démuth B. Keglevich G. Grün A. Drahos L. Sóti PL. Bakó P. Tetrahedron: Asymmetry 2014; 25: 141
76b Bakó P. Rapi Z. Keglevich G. Szabó T. Sóti PL. Vígh T. Grün A. Holczbauer T. Tetrahedron Lett. 2011; 52: 1473

77 Sóti PL. Telkes L. Rapi Z. Tóth A. Vígh T. Nagy ZK. Bakó P. Marosi G. J. Inorg. Organomet. Polym. 2014; 24: 713
78 Rapi Z. Bakó P. Drahos L. Keglevich G. Heteroat. Chem. 2015; 26: 63
79 Pálvölgyi Á. Rapi Z. Ozohanics O. Tóth G. Keglevich G. Bakó P. Res. Chem. Intermed. 2018; 44: 1627
80 Nemcsok T. Rapi Z. Keglevich G. Grün A. Bakó P. Chirality 2018; 30: 407
81 Rapi Z. Grün A. Keglevich G. Stirling A. Bakó P. New J. Chem. 2016; 40: 7856
82 Bakó P. Rapi Z. Grün A. Nemcsok T. Hegedűs L. Keglevich G. Synlett 2015; 26: 1847
83 Rapi Z. Grün A. Nemcsok T. Hessz D. Kállay M. Kubinyi M. Keglevich G. Bakó P. Tetrahedron: Asymmetry 2016; 27: 960

84a Perrard T. Plaquevent L.-C. Desmurs J.-R. Hebrault D. Org. Lett. 2000; 2: 2959
84b Ooi T. Ohara D. Fukumoto K. Maruoka K. Org. Lett. 2005; 7: 3195
84c Jayaraman S. Kumaraguru D. Arockiam JB. Paulpandian S. Rajendiran B. Siva A. Synlett 2014; 25: 1685

85a Loupy A. Sansoulet J. Zaparucha A. Merienne C. Tetrahedron Lett. 1989; 30: 333
85b Mirza-Aghayan M. Etemad-Moghadam G. Zaparucha A. Berlan J. Loupy A. Koenig M. Tetrahedron: Asymmetry 1995; 6: 2643

86 Yasuda K. Shindo M. Koga K. Tetrahedron Lett. 1996; 37: 6343
87 Rapi Z. Nemcsok T. Grün A. Pálvölgyi Á. Samu G. Hessz D. Kubinyi M. Kállay M. Keglevich G. Bakó P. Tetrahedron 2018; 74: 3512

88a Herchl R. Waser M. Tetrahedron Lett. 2013; 54: 2472
88b Herchl R. Waser M. Tetrahedron 2014; 70: 1935

For selected examples see:

89a Iseki K. Nagai T. Kobayashi Y. Tetrahedron Lett. 1994; 35: 3137
89b Caron S. Do NM. Arpin P. Larivée A. Synthesis 2003; 1693
89c Mizuta S. Shibata N. Hibino M. Nagano S. Nakamura S. Toru T. Tetrahedron 2007; 63: 8521
89d Hu X. Wang J. Li W. Lin L. Liu X. Feng X. Tetrahedron Lett. 2009; 50: 4378
89e Zhao H. Qin B. Liu X. Feng X. Tetrahedron 2007; 63: 6822

For improved procedures using tetramethylammonium fluoride as a source of fluoride ion, see:

90a Mizuta S. Shibata N. Akiti S. Fujimoto H. Nakamura S. Toru T. Org. Lett. 2007; 9: 3707
90b Kawai H. Tachi K. Tokunaga E. Shiro M. Shibata N. Org. Lett. 2010; 12: 5104
90c Kawai H. Mizuta S. Tokunaga E. Shibata N. J. Fluorine Chem. 2013; 152: 46

91 Kawai H. Kusuda A. Mizuta S. Nakamura S. Funahashi Y. Masuda H. Shibata N. J. Fluorine Chem. 2009; 130: 762
92 Szabó GT. Aranyosi K. Csiba M. Tőke L. Synthesis 1987; 565
93 Ooi T. Kato D. Inamura K. Ohmatsu K. Maruoka K. Org. Lett. 2007; 9: 3945
94 Ho C.-Y. Chen Y.-C. Wong M.-K. Yang D. J. Org. Chem. 2005; 70: 898
95 Aggarwal VK. Lopin C. Sandrinelli F. J. Am. Chem. Soc. 2003; 125: 7596

For selected examples, see:

96a Chen M. Hartwig JF. Angew. Chem. Int. Ed. 2014; 53: 12172
96b Kennedy CR. Guidera JA. Jacobsen JN. ACS Cent. Sci. 2016; 2: 416
96c Izquierdo J. Orue A. Scheidt KA. J. Am. Chem. Soc. 2013; 135: 10634
96d Lacour J. Monchaud D. Marsol C. Tetrahedron Lett. 2002; 43: 8257

97 Simon RJ. Kania RS. Zuckermann RN. Huebner VD. Jewell DA. Banville S. Ng S. Wang L. Rosenberg S. Marlowe CK. Spellmeyer DC. Tan R. Frankel AD. Santi DV. Cohen FE. Bartlett PA. Proc. Natl. Acad. Sci. U. S. A. 1992; 89: 9367

For reviews, see:

98a Gangloff N. Ulbricht J. Lorson T. Schlaad H. Luxenhofer R. Chem. Rev. 2016; 116: 1753
98b Seo J. Lee B.-C. Zuckermann RN. In Comprehensive Biomaterials. Ducheyne P. Healy KE. Hutmacher DW. Grainger DW. Kirkpatrick CJ. Elsevier; Amsterdam: 2011. 1st ed., Vol. 2 53
98c Fowler SA. Blackwell HE. Org. Biomol. Chem. 2009; 7: 1508
98d Culf AS. Ouellette RJ. Molecules 2010; 15: 5282

For reviews, see:

99a Webster AM. Cobb SL. Chem.–Eur. J. 2018; 24: 7560
99b Yoo B. Shin SB. Y. Huang ML. Kirshenbaum K. Chem.–Eur. J. 2010; 16: 5528

100 Shin SB. Y. Yoo B. Todaro LJ. Kirshenbaum K. J. Am. Chem. Soc. 2007; 129: 3218

101a Huang ML. Shin SB. Y. Benson MA. Torres VJ. Kirshenbaum K. ChemMedChem 2012; 7: 114
101b Comegna D. Benincasa M. Gennaro R. Izzo I. De Riccardis F. Bioorg. Med. Chem. 2010; 18: 2010

102a Howard E. Cousido-Siah A. Lepage ML. Schneider JP. Bodlenner A. Mitschler A. Meli A. Izzo I. Alvarez HA. Podjarny A. Compain P. Angew. Chem. Int. Ed. 2018; 57: 8002
102b Lepage ML. Schneider JP. Bodlenner A. Meli A. De Riccardis F. Schmitt M. Tarnus C. Nguyen-Huynh N.-T. Francois Y.-N. Leize-Wagner E. Birck C. Cousido-Siah A. Podjarny A. Izzo I. Compain P. Chem.–Eur. J. 2016; 22: 1
102c Lepage ML. Meli A. Bodlenner A. Tarnus C. De Riccardis F. Izzo I. Compain P. Beilstein J. Org. Chem. 2014; 10: 1406

103a De Cola C. Licen S. Comegna D. Cafaro E. Bifulco G. Izzo I. Tecilla P. De Riccardis F. Org. Biomol. Chem. 2009; 7: 2851
103b D’Amato A. Volpe R. Vaccaro MC. Terracciano S. Bruno I. Tosolini M. Tedesco C. Pierri G. Tecilla P. Costabile C. DellaSala G. Izzo I. De Riccardis F. J. Org. Chem. 2017; 82: 8848

104a Maulucci N. Izzo I. Bifulco G. Aliberti A. De Cola C. Comegna D. Gaeta C. Napolitano A. Pizza C. Tedesco C. Flot D. De Riccardis F. Chem. Commun. 2008; 3927
104b Izzo I. Ianniello G. De Cola C. Nardone B. Erra L. Vaughan G. Tedesco C. De Riccardis F. Org. Lett. 2013; 15: 598
104c De Cola C. Fiorillo G. Meli A. Aime S. Gianolio E. Izzo I. De Riccardis F. Org. Biomol. Chem. 2014; 12: 424
104d D’Amato A. Della Sala G. Izzo I. Costabile C. Masuda Y. De Riccardis F. Molecules 2018; 23: 1779

105 Della Sala G. Nardone B. De Riccardis F. Izzo I. Org. Biomol. Chem. 2013; 11: 726

106a D’Amato A. Pierri G. Costabile C. Della Sala G. Tedesco C. Izzo I. De Riccardis F. Org. Lett. 2018; 20: 640
106b D’Amato A. Schettini R. Della Sala G. Costabile C. Tedesco C. Izzo I. De Riccardis F. Org. Biomol. Chem. 2017; 15: 9932

107 Schettini R. Costabile C. Della Sala G. Buirey J. Tosolini M. Tecilla P. Vaccaro MC. Bruno I. De Riccardis F. Izzo I. Org. Biomol. Chem. 2018; 16: 6708
108 Schettini R. Nardone B. De Riccardis F. Della Sala G. Izzo I. Eur. J. Org. Chem. 2014; 7793
109 Schettini R. De Riccardis F. Della Sala G. Izzo I. J. Org. Chem. 2016; 81: 2494
110 Respondek T. Cueny E. Kodanko J. Org. Lett. 2012; 14: 150
111 Schettini R. D’Amato A. De Riccardis F. Della Sala G. Izzo I. Synthesis 2017; 49: 1319

112a Jew S.-s. Lee Y.-J. Lee J. Kang MJ. Jeong B.-S. Lee J.-H. Yoo M.-S. Kim M.-J. Choi S.-h. Ku J.-M. Park H.-g. Angew. Chem. Int. Ed. 2004; 43: 2382
112b Nakayama K. Maruoka K. Tetrahedron Lett. 2008; 49: 5461
112c Lee Y.-J. Lee J. Kim M.-J. Kim T.-S. Park H.-g. Jew S.-s. Org. Lett. 2005; 7: 1557

113 Boyle GA. Govender T. Kruger HG. Maguire GE. M. Tetrahedron: Asymmetry 2004; 15: 3775

114a Calixarenes and Beyond. Neri P. Sessler PJ. L. Wang M.-X. Springer; Dordrecht: 2016
114b Gutsche CD. Calixarenes, an Introduction. Royal Society of Chemistry; Cambridge: 2008
114c Calixarenes 2001. Asfari Z. Böhmer V. Harrowfield J. Vicens J. Kluwer; Dordrecht: 2001
114d Calixarenes in the Nanoworld. Vicens J. Harrowfield J. Springer; Dordrecht: 2007

115a Taniguchi H. Nomura E. Chem. Lett. 1988; 17: 1773
115b Nomura E. Taniguchi H. Kawaguchi K. Otsuji Y. Chem. Lett. 1991; 20: 2167
115c Taniguchi H. Kawaguchi K. Otsuji Y. J. Org. Chem. 1993; 58: 4709
115d Araki K. Yanagi A. Shinkai S. Tetrahedron 1993; 49: 6763
115e Yang F. Wang Y. Guo H. Xie J. Liu Z. Can. J. Chem. 2010; 88: 622

116a Bozkurt S. Durmaz M. Yilmaz M. Sirit A. Tetrahedron: Asymmetry 2008; 19: 618
116b Shimizu S. Shirakawa S. Eur. J. Org. Chem. 2009; 1916
116c Shirakawa S. Shimizu S. New J. Chem. 2010; 34: 1217
116d Su W. Jin C. Huang L. J. Chem. Res. 2012; 36: 532

117 De Simone NA. Schettini R. Talotta C. Gaeta C. Izzo I. Della Sala G. Neri P. Eur. J. Org. Chem. 2017; 5649