Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

Abstract

Trichloroacetamides can act as radical precursors to synthesize nitrogen-containing heterocycles in a variety of processes, mainly involving atom transfer radical cyclizations (ATRC), mediated by Cu(I) or Ru(II) catalysts, and the hydride reductive method, employing either Bu₃SnH or (Me₃Si)₃SiH, or recently NaBH₃CN. Additionally, amine-mediated single-electron transfer cyclizations, as well as radical processes promoted by Ni, Fe, Mn, Ti, and Ag, have been developed.

1 Introduction

2 Atom Transfer Radical Cyclizations (ATRC)

2.1 Copper-Mediated Reactions

2.2 Ruthenium(II)-Mediated Reactions

2.3 ATRC Promoted by Other Metals

3 Photocyclization Reactions

4 Reductive Cyclization via Single-Electron Transfer Processes

4.1 Ni/AcOH-Promoted Cyclizations

4.2 Titanocene(III)-Catalyzed Reactions

4.3 Silver Acetate Mediated Reactions

4.4 Amine-Mediated Single-Electron Transfer

5 Cyclization Involving M–H Hydrogen Atom Donors (M = Sn, Si, B)

5.1 Bu₃SnH-Mediated Reactions

5.2 (Me₃Si)₃SiH (TTMSS)-Mediated Reactions

5.3 Borohydride-Mediated Radical Cyclizations

6 Concluding Remarks

Key words

radical reactions - lactams - cyclization - nitrogen heterocycles - hydrides - atom transfer - reduction - haloacetamides

• References

• 1 Present Address: Uriach, Avgda Camí Reial 51-57, 08184 Palau-solità i Plegamans, Barcelona (Spain).
• 2a Clark AJ. Chem. Soc. Rev. 2002; 31: 1
• 2b Eckenhoff WT, Pintauer T. Catal. Rev. 2010; 52: 1
• 2c Pintauer T. Eur. J. Inorg. Chem. 2010; 2449
• 2d Clark AJ. Eur. J. Org. Chem. 2016; 2231
• 3 Giese B, Kopping B, Göbel T, Dickhaut J, Thoma G, Kulicke KJ, Trach F. Org. React. 1995; 48: 301
• 4a Broggi J, Terme T, Vanelle P. Angew. Chem. Int. Ed. 2014; 53: 384
• 4b Zhang N, Samanta SR, Rosen BM, Percec V. Chem. Rev. 2014; 114: 5848

For selected books on radicals in organic synthesis, see:
• 5a Radicals in Organic Synthesis . Vol. 2. Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001
• 5b Togo H. Advanced Free Radical Reactions for Organic Synthesis. Elsevier; Amsterdam: 2003
• 5c Zard SZ. Radical Reactions in Organic Synthesis . Oxford University Press; Oxford: 2003
• 6 Nagashima H, Wakamatsu H, Itoh K. J. Chem. Soc., Chem. Commun. 1984; 652
• 7 For a comprehensive review, see: Overman LE, Carpenter NE. In Organic Reactions . Overman LE. Hoboken; Wiley: 2005. 66 1
• 8 Broadhurst MD. US Patent 4132713, 1977
• 9 Nagashima H, Ara K.-I, Wakamatsu H, Itoh K. J. Chem. Soc., Chem. Commun. 1985; 518
• 10 Hirai Y, Hagiwara A, Terada T, Yamazaki T. Chem. Lett. 1987; 2417
• 11 Seijas JA, Vázquez-Tato MP, Castedo L, Estévez RJ, Ónega MG, Ruíz M. Tetrahedron 1992; 48: 1637
• 12 Pattarozzi M, Roncaglia F, Giangiordano V, Davoli P, Prati F, Ghelfi F. Synthesis 2010; 694
• 13 Cornia A, Felluga F, Frenna V, Ghelfi F, Pagnoni UM, Parsons AF, Petrillo G, Spinelli D. Synthesis 2011; 8: 1267
• 14a Nagashima H, Ozaki N, Seki K, Ishii M, Itoh K. J. Org. Chem. 1989; 54: 4497
• 14b Nagashima H, Ozaki N, Ishii M, Seki K, Washiyama M, Itoh K. J. Org. Chem. 1993; 58: 464
• 15 Iwamatsu S.-I, Matsubara K, Nagashima H. J. Org. Chem. 1999; 64: 9625

For steric and electronic influences of the N-substituent on the ratio of rotamers, see:
• 16a Stork G, Mah R. Heterocycles 1989; 28: 723
• 16b Bartuschat AL, Wicht K, Heinrich MR. Angew. Chem. Int. Ed. 2015; 54: 10294
• 16c Clark AJ, Curran DP, Fox DJ, Ghelfi F, Guy CS, Hay B, James N, Phillips JM, Roncaglia F, Sellars PB, Wilson P, Zhang H. J. Org. Chem. 2016; 81: 5547
• 17 Iwamatsu S.-I, Kondo H, Matsubara K, Nagashima H. Tetrahedron 1999; 55: 1687
• 18 For radical domino reactions in organic synthesis, see: Sebre LJ, Devery III JJ, Stephenson CR. J. ACS Catal. 2014; 4: 703
• 19a Davies DT, Kapur N, Parsons AF. Tetrahedron Lett. 1999; 40: 8615
• 19b Davies DT, Kapur N, Parsons AF. Tetrahedron 2000; 56: 3941
• 20 Bryans JS, Chessum NE. A, Parsons AF, Ghelfi F. Tetrahedron Lett. 2001; 42: 2901
• 21 Bryans JS, Chessum NE. A, Huther N, Parsons AF, Ghelfi F. Tetrahedron 2003; 59: 6221
• 22a Benedetti M, Forti L, Ghelfi F, Pagnoni UM, Ronzoni R. Tetrahedron 1997; 14031
• 22b Ghelfi F, Bellesia F, Ghirardini G, Grandi R, Libertini E, Montemaggi MC, Pagnoni UM, Pinetti A, De Buyck L, Parsons AF. Tetrahedron 1999; 55: 5839
• 22c Pattarozzi M, Roncaglia F, Accorsi L, Parsons AF, Ghelfi F. Tetrahedron 2010; 66: 1357
• 23 Ghelfi F, Parsons AF. J. Org. Chem. 2000; 65: 6249
• 24 Bregoli M, Felluga F, Frenna V, Ghelfi F, Parsons AF, Pattarozzi M, Roncaglia F, Spinelli D. Tetrahedron 2012; 68: 5863
• 25a Stevens CV, Van Meenen E, Eeckhout Y, Vanderhoydonck B, Hooghe W. Chem. Commun. 2005; 4827
• 25b Stevens CV, Van Meenen E, Masschelein KG. R, Eeckhout Y, Hooghe W, D’hondt B, Nemykin VN, Zhdankin VZ. Tetrahedron Lett. 2007; 48: 7108
• 26a Clark AJ, Filik RP, Haddleton DM, Radigue A, Sanders CJ, Thomas GH, Smith ME. J. Org. Chem. 1999; 64: 8954
• 26b Clark AJ, Geden JV, Thom S. J. Org. Chem. 2006; 71: 1471
• 27 Clark AJ, Dell CP, Ellard JM, Hunt NA, McDonagh JP. Tetrahedron Lett. 1999; 40: 8619
• 28 Clark AJ, Battle GM, Heming AM, Haddleton DM, Bridge A. Tetrahedron Lett. 2001; 42: 2003
• 29 Motoyama Y, Kamo K, Yuasa A, Nagashima H. Chem. Commun. 2010; 46: 2256
• 30 Clark AJ, De Campo F, Deeth RJ, Filik RP, Gatard S, Hunt NA, Lastécouères D, Thomas GH, Verlhac J, Wongtap H. J. Chem. Soc., Perkin Trans. 1 2000; 671
• 31 Geden JV, Clark AJ, Coles SR, Guy CS, Ghelfi F, Thom S. Tetrahedron Lett. 2016; 57: 3109
• 32 Clark AJ, Geden JV, Thom S, Wilson P. J. Org. Chem. 2007; 72: 5923
• 33 Ram RN, Soni VK. Adv. Synth. Catal. 2016; 358: 276
• 34 Bull JA, Hutchings MG, Luján C, Quayle P. Tetrahedron Lett. 2008; 49: 1352
• 35a Clark AJ, Coles SR, Collis A, Debure T, Guy C, Murphy NP, Wilson P. Tetrahedron Lett. 2009; 50: 5609
• 35b Clark AJ, Coles SR, Collis A, Fullaway DR, Murphy NP, Wilson P. Tetrahedron Lett. 2009; 50: 6311
• 36 Diaba F, Montiel JA, Martinez-Laporta A, Bonjoch J. Tetrahedron Lett. 2013; 54: 2619
• 37a Pintauer T, Matyjaszewski K. Chem. Soc. Rev. 2008; 37: 1087
• 37b Balili MN. C, Pintauer T. Inorg. Chem. 2010; 49: 5642
• 38 Clark AJ, Duckmanton JN, Felluga F, Gennaro A, Ghelfi F, Hardiman JR. D, Isse AA, Manferdini C, Spinelli D. Eur. J. Org. Chem. 2016; 2479
• 39a Casaroli R, Felluga F, Frenna V, Ghelfi F, Pagnoni UM, Parsons AF, Spinelli D. Tetrahedron 2011; 67: 408
• 39b Bellesia F, Clark AJ, Felluga F, Gennaro A, Isse AA, Roncaglia F, Ghelfi F. Adv. Synth. Catal. 2013; 355: 1649
• 39c Clark AJ, Cornia A, Felluga F, Gennaro A, Ghelfi F, Isse AA, Menziani MC, Muniz-Miranda F, Roncaglia F, Spinelli D. Eur. J. Org. Chem. 2014; 6734
• 40a Diaba F, Martínez-Laporta A, Bonjoch J, Pereira A, Muñoz-Molina JM, Pérez PJ, Belderrain TR. Chem. Commun. 2012; 8799
• 40b Diaba F, Martínez-Laporta A, Coussanes G, Fernández I, Bonjoch J. Tetrahedron 2015; 71: 3642
• 41 Nagashima H, Wakamatsu H, Ozaki N, Ishii T, Watanabe M, Tajima T, Itoh K. J. Org. Chem. 1992; 57: 1682
• 42 Rachita MA, Slough GA. Tetrahedron Lett. 1993; 34: 6821
• 43 Swift MD, Donaldson A, Sutherland A. Tetrahedron Lett. 2009; 50: 3241
• 44 Li Q, Li G, Ma S, Feng P, Shi Y. Org. Lett. 2013; 15: 2601
• 45a Nagashima H, Gondo M, Masuda S, Kondo H, Yamaguchi Y, Matsubara K. Chem. Commun. 2003; 442
• 45b Motoyama Y, Hanada S, Shimamoto K, Nagashima H. Tetrahedron 2006; 62: 2779
• 46a Dutta B, Scopelliti R, Severin K. Organometallics 2008; 27: 423
• 46b Wolf J, Thommes K, Briel O, Scopelliti R, Severin K. Organometallics 2008; 27: 4464
• 47 Tallarico JA, Malnick LM, Snapper ML. J. Org. Chem. 1999; 64: 344
• 48 Quayle P, Fengas D, Richards S. Synlett 2003; 1797
• 49 Diaba F, Martínez-Laporta A, Bonjoch J. J. Org. Chem. 2014; 79: 9365
• 50 Seigal BA, Fajardo C, Snapper ML. J. Am. Chem. Soc. 2005; 127: 16329
• 51 Edlin CD, Faulkner J, Quayle P. Tetrahedron Lett. 2006; 47: 1145
• 52 Borguet Y, Sauvage X, Zaragoza G, Demonceau A, Delaude L. Beilstein J. Org. Chem. 2010; 6: 1167
• 53a McGonagle FI, Brown L, Cooke A, Sutherland A. Org. Biomol. Chem. 2010; 8: 3418
• 53b McGonagle FI, Brown L, Cooke A, Sutherland A. Tetrahedron Lett. 2011; 52: 2330
• 54a Gordon E.; DE2612731A1, 1976.
• 54b Gordon E.; FR2305434A1, 1976.
• 55 Benedetti M, Forti L, Ghelfi F, Pagnoni UM, Ronzoni R. Tetrahedron 1997; 53: 14031
• 56 Forti L, Ghelfi F, Libertini E, Pagnoni UM, Soragni E. Tetrahedron 1997; 53: 17761
• 57a Gilbert BC, Kalz W, Lindsay CI, McGrail PT, Parsons AF, Whittaker DT. E. Tetrahedron Lett. 1999; 40: 6095
• 57b Huther N, McGrail PT, Parsons AF. Eur. J. Org. Chem. 2004; 1740
• 58 Beck AL, Mascal M, Moody CJ, Slawin AM. Z, Williams DJ, Coates WJ. J. Chem. Soc., Perkin Trans. 1 1992; 797
• 59 For a review on the Witkop cyclization, see: Gritsch PJ, Leitner C, Pfaffenbach M, Gaich T. Angew. Chem. Int. Ed. 2014; 53: 1208
• 60 Boivin J, Yousfi M, Zard SZ. Tetrahedron Lett. 1994; 35: 5629
• 61a Quiclet-Sire B, Saunier J.-B, Zard SZ. Tetrahedron Lett. 1996; 37: 1397
• 61b Cassayre J, Quiclet-Sire B, Saunier J.-B, Zard SZ. Tetrahedron 1998; 54: 1029
• 62 Cassayre J, Dauge D, Zard SZ. Synlett 2000; 471
• 63 Boivin J, Yousfi M, Zard SZ. Tetrahedron Lett. 1994; 35: 9553
• 64 Boivin J, Yousfi M, Zard SZ. Tetrahedron Lett. 1997; 38: 5985
• 65 Cassayre J, Quiclet-Sire B, Saunier J.-B, Zard SZ. Tetrahedron Lett. 1998; 39: 8995
• 66 Cassayre J, Zard SZ. Synlett 1999; 501
• 67 Cassayre J, Zard SZ. J. Organomet. Chem. 2001; 624: 316
• 68 For a review on HAT, see: Nechab M, Mondal S, Bertrand MP. Chem. Eur. J. 2014; 20: 16034
• 69 Justicia J, Álvarez de Cienfuegos L, Campaña AG, Miguel D, Jakoby V, Gansäuer A, Cuerva JM. Chem. Soc. Rev. 2011; 40: 3525
• 70 Diaba F, Gómez-Bengoa E, Cuerva JM, Bonjoch J, Justicia J. RSC Adv. 2016; 6: 55360

For mechanistic studies of the hydrogen atom transfer process from THF, see:
• 71a Jin J, Newcomb M. J. Org. Chem. 2008; 73: 7901
• 71b Paradas M, Campaña AG, Jiménez T, Robles R, Oltra JE, Buñuel E, Justicia J, Cárdenas DJ, Cuerva JM. J. Am. Chem. Soc. 2010; 132: 12748
• 72 Doi N, Takeda N, Miyata O, Ueda M. J. Org. Chem. 2016; 81: 7855
• 73 Naito T, Saito A, Ueda M, Miyata O. Heterocycles 2005; 65: 1857
• 74 Ishibashi H, Haruki S, Uchiyama M, Tamura O, Matsuo J.-I. Tetrahedron Lett. 2006; 47: 6263
• 75 Ishibashi H, Sasaki M, Taniguchi T. Tetrahedron 2008; 64: 7771
• 76 Taniguchi T, Kawajiri R, Ishibashi H. ARKIVOC 2008; (xiv): 7
• 77 Taniguchi T, Sasaki M, Ishibashi H. Heterocycles 2010; 80: 657
• 78a Parsons AF, Taylor RJ. K. J. Chem. Soc., Chem. Commun. 1993; 1224
• 78b Parsons AF, Taylor RJ. K. J. Chem. Soc., Perkin Trans. 1 1994; 1945
• 78c Bryans JS, Large JM, Parsons AF. Tetrahedron Lett. 1999; 40: 3487
• 79a Goodall K, Parsons AF. Tetrahedron 1996; 52: 6739
• 79b Bryans JS, Large JM, Parsons AF. J. Chem. Soc., Perkin Trans. 1 1999; 2897
• 80a Ishibashi H, Higuchi M, Ohba M, Ikeda M. Tetrahedron Lett. 1998; 39: 75
• 80b Ishibashi H, Kodama K, Higuchi M, Muraoka O, Tanabe G, Takeda Y. Tetrahedron 2001; 57: 7629
• 80c Ikeda M, Ohtani S, Yamamoto T, Sato T, Ishibashi H. J. Chem. Soc., Perkin Trans. 1 1998; 1763
• 81 Quirante J, Escolano C, Diaba F, Bonjoch J. J. Chem. Soc., Perkin Trans. 1 1999; 1157
• 82a Quirante J, Diaba F, Vila X, Bonjoch J, Lago E, Molins E. C. R. Acad. Sci. Paris 2001; 4: 513
• 82b Marin ML, Zaragoza RJ, Miranda MA, Diaba F, Bonjoch J. Org. Biomol. Chem. 2011; 9: 3180

For memory of chirality (MOC) in radical cyclizations, inter alia, see:
• 83a Curran DP, Liu WD, Chen CH. T. J. Am. Chem. Soc. 1999; 121: 11012
• 83b Dalgard JE, Rychnovsky SD. Org. Lett. 2004; 6: 2713
• 83c Zhao H, Hsu DC, Carlier PR. Synthesis 2005; 1
• 83d Gloor CS, Dénès F, Renaud P. Free Radical Res 2016; in press; DOI: 10.1080/10715762.2016.1232485.
• 84 Diaba F, Montiel JA, Bonjoch J. Tetrahedron 2013; 69: 4883
• 85 Vila X, Quirante J, Paloma L, Bonjoch J. Tetrahedron Lett. 2004; 45: 4661
• 86 Quirante J, Vila X, Paloma L, Guiu JM, Bonjoch J. Tetrahedron 2007; 63: 1372
• 87 Quirante J, Escolano C, Diaba F, Bonjoch J. Heterocycles 1999; 50: 731
• 88 Quirante J, Escolano C, Costejà L, Bonjoch J. Tetrahedron Lett. 1997; 38: 6901
• 89 Quirante J, Escolano C, Massot M, Bonjoch J. Tetrahedron 1997; 53: 1391
• 90a Quirante J, Escolano C, Bosch J, Bonjoch J. J. Chem. Soc., Chem. Commun. 1995; 2141
• 90b Quirante J, Escolano C, Merino A, Bonjoch J. J. Org. Chem. 1998; 63: 968
• 91 Quirante J, Torra M, Diaba F, Escolano C, Bonjoch J. Tetrahedron: Asymmetry 1999; 10: 2399
• 92 Diaba F, Montiel JA, Bonjoch J. Chem. Commun 2016; 52: 14031
• 93 Barltrop JA, Bradbury D. J. Am. Chem. Soc. 1973; 95: 5085
• 94a For a review on borohydrides in radical chemistry, see: Kawamoto T, Ryu I. Org. Biomol. Chem. 2014; 12: 9733
• 94b For mechanistic studies, see: Kawamoto T, Uehara S, Hirao H, Fukuyama T, Matsubara H, Ryu I. J. Org. Chem. 2014; 79: 3999
• 95 Coussanes G. Ph.D. Dissertation. University of Barcelona; Spain: 2016
• 96a Watanabe Y, Ueno Y, Tanaka C, Okawara M, Endo T. Tetrahedron Lett. 1987; 28: 3953
• 96b Ram RN, Gupta DK. Adv. Synth. Catal. 2016; 358: 3254
• 97a Lee GM, Weinreb SM. J. Org. Chem. 1990; 55: 1281
• 97b Brill ZC, Grover HK, Maimone TJ. Science 2016; 352: 1078
• 98a Nagashima H, Wakamatsu H, Itoh K, Tomo Y, Tsuji J. Tetrahedron Lett. 1983; 24: 2395
• 98b Takano S, Nishizawa S, Akiyama M, Ogasawara K. Heterocycles 1984; 22: 1779
• 98c Helliwell M, Fengas D, Knight CK, Parker J, Quayle P, Raftery J, Richards SN. Tetrahedron Lett. 2005; 46: 7129