1.1 Metal-Catalyzed Intramolecular Coupling Reactions

S. Gao; D. Wang

doi:10.1055/sos-SD-221-00001

Share / Bookmark

Facebook X Linkedin Weibo

Gao, S. et al.: 2016 Science of Synthesis, 2016/4a: Metal-Catalyzed Cyclization Reactions 1 DOI: 10.1055/sos-SD-221-00001

Metal-Catalyzed Cyclization Reactions 1

1.1 Metal-Catalyzed Intramolecular Coupling Reactions

More Information

Book

Editors: Gao, S.; Ma, S.

Authors: Alderson, J.; Beccalli, E. M.; Bonetti, A.; Gao, S.; Guiry, P.; Jammi, S.; Mazza, A.; Nottingham, C.; Phelps, A.; Schomaker, J. M.; Shi, M.; Tang, X.-Y.; Wang, D.; Yamamoto, Y.; You, S. ; Zhang, L.; Zhang, X.

Title: Metal-Catalyzed Cyclization Reactions 1

Print ISBN: 9783131998613; Online ISBN: 9783132403406; Book DOI: 10.1055/b-003-129294

1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at

Preview
Abstract
Full Text
References
Supplementary Material

Abstract

This chapter presents metal-catalyzed or -promoted intramolecular cross-coupling reactions for C—C bond formation in the preparation of cyclic compounds. Examples of synthetic applications in natural products syntheses are discussed to illustrate the potential of these methodologies.

Key words

cross coupling - reductive coupling - intramolecular coupling - C—C bond formation - palladium - chromium - copper - nickel - Suzuki–Miyaura coupling - Stille coupling - Negishi coupling - Sonogashira coupling - Hiyama coupling - dehydrogenative coupling - Nozaki–Hiyama–Kishi coupling - ene–yne coupling

1 Miyaura N, Yanagi T, Suzuki A. Synth. Commun. 1981; 11: 513

Search in Google Scholar

2 Suzuki A. J. Organomet. Chem. 1999; 576: 147

Crossref Search in Google Scholar

3 Braga AAC, Morgon NH, Ujaque G, Maseras F. J. Am. Chem. Soc. 2005; 127: 9298

PubMed Search in Google Scholar

4 Miyaura N. J. Organomet. Chem. 2002; 653: 54

Search in Google Scholar

5 Chemler SR, Trauner D, Danishefsky SJ. Angew. Chem. Int. Ed. 2001; 40: 4544

PubMed Search in Google Scholar

6 Miyaura N, Ishiyama T, Ishikawa M, Suzuki A. Tetrahedron Lett. 1986; 27: 6369

Search in Google Scholar

7 Miyaura N, Ishiyama T, Sasaki H, Ishikawa M, Satoh M, Suzuki A. J. Am. Chem. Soc. 1989; 111: 314

Search in Google Scholar

8 Miyaura N, Ishikawa M, Suzuki A. Tetrahedron Lett. 1992; 33: 2571

Search in Google Scholar

9 Kwochka WR, Damrauer R, Schmidt MW, Gordon MS. Organometallics 1994; 13: 3728

Search in Google Scholar

10 Smith BB, Kwochka WR, Swope RJ, Smyth JR. J. Org. Chem. 1997; 62: 8589

PubMed Search in Google Scholar

11 Chemler SR, Danishefsky SJ. Org. Lett. 2000; 2: 2695

PubMed Search in Google Scholar

12 Frank SA, Chen H, Kunz RK, Schnaderbeck MJ, Roush WR. Org. Lett. 2000; 2: 2691

PubMed Search in Google Scholar

13 Uenishi J.-i, Beau J.-M, Armstrong RW, Kishi Y. J. Am. Chem. Soc. 1987; 109: 4756

Search in Google Scholar

14 Humphrey JM, Aggen JB, Chamberlin AR. J. Am. Chem. Soc. 1996; 118: 11759

Search in Google Scholar

15 Williams DR, Walsh MJ, Miller NA. J. Am. Chem. Soc. 2009; 131: 9038

PubMed Search in Google Scholar

16 Carbonnelle AC, Zhu J. Org. Lett. 2000; 2: 3477

PubMed Search in Google Scholar

17 Dufour J, Neuville L, Zhu J. Chem.–Eur. J. 2010; 16: 10523

PubMed Search in Google Scholar

18 Wang Z, Bois-Choussy M, Jia Y, Zhu J. Angew. Chem. Int. Ed. 2010; 49: 2018

PubMed Search in Google Scholar

19 Jia Y, Bois-Choussy M, Zhu J. Angew. Chem. Int. Ed. 2008; 47: 4167

PubMed Search in Google Scholar

20 Wu B, Liu QS, Sulikowski GA. Angew. Chem. Int. Ed. 2004; 43: 6673

PubMed Search in Google Scholar

21 Ghidu VP, Wang JQ, Wu B, Liu QS, Jacobs A, Marnett LJ, Sulikowski GA. J. Org. Chem. 2008; 73: 4949

PubMed Search in Google Scholar

22 Tortosa M, Yakelis NA, Roush WR. J. Am. Chem. Soc. 2008; 130: 2722

PubMed Search in Google Scholar

23 Tortosa M, Yakelis NA, Roush WR. J. Org. Chem. 2008; 73: 9657

PubMed Search in Google Scholar

24 Milstein D, Stille JK. J. Am. Chem. Soc. 1978; 100: 3636

Search in Google Scholar

25 Milstein D, Stille JK. J. Am. Chem. Soc. 1979; 101: 4992

Search in Google Scholar

26 Stille JK. Angew. Chem. Int. Ed. Engl. 1986; 25: 508

Crossref Search in Google Scholar

27 Echavarren AM, Stille JK. J. Am. Chem. Soc. 1987; 109: 5478

Search in Google Scholar

28 Han X, Stoltz BM, Corey EJ. J. Am. Chem. Soc. 1999; 121: 7600

Crossref Search in Google Scholar

29 Piers E, Friesen RW, Keay BA. J. Chem. Soc., Chem. Commun. 1985; 809

30 Piers E, Lu Y.-F. J. Org. Chem. 1988; 53: 926

Search in Google Scholar

31 Piers E, Friesen RW. J. Org. Chem. 1986; 51: 3405

Search in Google Scholar

32 Stille JK, Tanaka M. J. Am. Chem. Soc. 1987; 109: 3785

Search in Google Scholar

33 Nicolaou KC, Xu JY, Murphy F, Barluenga S, Baudoin O, Wei H.-X, Gray DL. F, Ohshima T. Angew. Chem. Int. Ed. 1999; 38: 2447

PubMed Search in Google Scholar

34 Garg NK, Hiebert S, Overman LE. Angew. Chem. Int. Ed. 2006; 45: 2912

PubMed Search in Google Scholar

35 Becker MH, Chua P, Downham R, Douglas CJ, Garg NK, Hiebert S, Jaroch S, Matsuoka RT, Middleton JA, Ng FW, Overman LE. J. Am. Chem. Soc. 2007; 129: 11987

PubMed Search in Google Scholar

36 Negishi E, Baba S. J. Chem. Soc., Chem. Commun. 1976; 597

37 Baba S, Negishi E. J. Am. Chem. Soc. 1976; 98: 6729

Crossref Search in Google Scholar

38 Negishi E, King AO, Okukado N. J. Org. Chem. 1977; 42: 1821

Search in Google Scholar

39 King AO, Okukado N, Negishi E. J. Chem. Soc., Chem. Commun. 1977; 683

40 King AO, Negishi E, Villani Jr. FJ, Silveira Jr. A. J. Org. Chem. 1978; 43: 358

Search in Google Scholar

41 Negishi E, Van Horn DE. J. Am. Chem. Soc. 1977; 99: 3168

Search in Google Scholar

42 Negishi E. Acc. Chem. Res. 1982; 15: 340

Search in Google Scholar

43 Negishi E, Anastasia L. Chem. Rev. 2003; 103: 1979

PubMed Search in Google Scholar

44 Nolasco L, Perez Gonzalez M, Caggiano L, Jackson RF. W. J. Org. Chem. 2009; 74: 8280

PubMed Search in Google Scholar

45 Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 4467

46 Sonogashira K, In Comprehensive Organic Synthesis Trost BM, Fleming I. Pergamon Oxford 1991; Vol. 3 521

Crossref

47 Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874

PubMed Search in Google Scholar

48 Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834

PubMed Search in Google Scholar

49 Chinchilla R, Nájera C. Chem. Soc. Rev. 2011; 40: 5084

PubMed Search in Google Scholar

50 Wang D, Gao S. Org. Chem. Front. 2014; 1: 556

Crossref Search in Google Scholar

51 Balraju V, Reddy RS, Periasamy M, Iqbal J. J. Org. Chem. 2005; 70: 9626

PubMed Search in Google Scholar

52 Mohapatra DK, Bhattasali D, Gurjar MK, Khan MI, Shashidhara KS. Eur. J. Org. Chem. 2008; 6213

53 Koyama Y, Lear MJ, Yoshimura F, Ohashi I, Mashimo T, Hirama M. Org. Lett. 2005; 7: 267

PubMed Search in Google Scholar

54 Yoshida J.-i, Tamao K, Takahashi M, Kumada M. Tetrahedron Lett. 1978; 2161

55 Yoshida J.-i, Tamao K, Yamamoto H, Kakui T, Uchida T, Kumada M. Organometallics 1982; 1: 542

Search in Google Scholar

56 Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918

Crossref Search in Google Scholar

57 Hiyama T, Hatanaka Y. Pure Appl. Chem. 1994; 66: 1471

Search in Google Scholar

58 Hatanaka Y, Hiyama T. Synlett 1991; 845

59 Sugiyama A, Ohnishi Y, Nakaoka M, Nakao Y, Sato H, Sakaki S, Nakao Y, Hiyama T. J. Am. Chem. Soc. 2008; 130: 12975

PubMed Search in Google Scholar

60 Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893

PubMed Search in Google Scholar

61 Denmark SE, Yang S.-M. J. Am. Chem. Soc. 2002; 124: 2102

PubMed Search in Google Scholar

62 Denmark SE, Yang S.-M. Org. Lett. 2001; 3: 1749

PubMed Search in Google Scholar

63 Denmark SE, Yang S.-M. J. Am. Chem. Soc. 2002; 124: 15196

PubMed Search in Google Scholar

64 Denmark SE, Yang S.-M. J. Am. Chem. Soc. 2004; 126: 12432

PubMed Search in Google Scholar

65 Moritani I, Fujiwara Y. Synthesis 1973; 524

66 Li C.-J. Acc. Chem. Res. 2009; 42: 335

PubMed Search in Google Scholar

67 Li Z, Bohle DS, Li C.-J. Proc. Natl. Acad. Sci. U. S. A. 2006; 103: 8928

PubMed Search in Google Scholar

68 Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318

PubMed Search in Google Scholar

69 Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215

PubMed Search in Google Scholar

70 Ferreira EM, Stoltz BM. J. Am. Chem. Soc. 2003; 125: 9578

PubMed Search in Google Scholar

71 Zhang H, Ferreira EM, Stoltz BM. Angew. Chem. Int. Ed. 2004; 43: 6144

PubMed Search in Google Scholar

72 Ferreira EM, Zhang H, Stoltz BM. Tetrahedron 2008; 64: 5987

PubMed Search in Google Scholar

73 Beck EM, Hatley R, Gaunt MJ. Angew. Chem. Int. Ed. 2008; 47: 3004

PubMed Search in Google Scholar

74 Garg NK, Caspi DD, Stoltz BM. J. Am. Chem. Soc. 2004; 126: 9552

PubMed Search in Google Scholar

75 Okude Y, Hirano S, Hiyama T, Nozaki H. J. Am. Chem. Soc. 1977; 99: 3179

Search in Google Scholar

76 Okude Y, Hiyama T, Nozaki H. Tetrahedron Lett. 1977; 3829

77 Jin H, Uenishi J.-i, Christ WJ, Kishi Y. J. Am. Chem. Soc. 1986; 108: 5644

Search in Google Scholar

78 Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H. J. Am. Chem. Soc. 1986; 108: 6048

PubMed Search in Google Scholar

79 Fürstner A, Shi N. J. Am. Chem. Soc. 1996; 118: 12349

Search in Google Scholar

80 Fürstner A, Shi N. J. Am. Chem. Soc. 1996; 118: 2533

Search in Google Scholar

81 Fürstner A. Chem. Rev. 1999; 99: 991

PubMed Search in Google Scholar

82 Aoyagi S, Wang T.-C, Kibayashi C. J. Am. Chem. Soc. 1993; 115: 11393

Search in Google Scholar

83 Bian J, Wingerden MV, Ready JM. J. Am. Chem. Soc. 2006; 128: 7428

PubMed Search in Google Scholar

84 Zhu W, Jiménez M, Jung W.-H, Camarco DP, Balachandran R, Vogt A, Day BW, Curran DP. J. Am. Chem. Soc. 2010; 132: 9175

PubMed Search in Google Scholar

85 Ciesielski J, Gandon V, Frontier AJ. J. Org. Chem. 2013; 78: 9541

PubMed Search in Google Scholar

86 Elliott MR, Dhimane A.-L, Malacria M. J. Am. Chem. Soc. 1997; 119: 3427

Search in Google Scholar

87 Roethle PA, Trauner D. Org. Lett. 2006; 8: 345

PubMed Search in Google Scholar

88 Ullmann F. Ber. Dtsch. Chem. Ges. 1903; 36: 2389

Search in Google Scholar

89 Ullmann F. Ber. Dtsch. Chem. Ges. 1904; 37: 853

Search in Google Scholar

90 Goldberg I. Ber. Dtsch. Chem. Ges. 1906; 39: 1691

Search in Google Scholar

91 Okuro K, Furuune M, Enna M, Miura M, Nomura M. J. Org. Chem. 1993; 58: 4716

Search in Google Scholar

92 Yu S, Liu F, Ma D. Tetrahedron Lett. 2006; 47: 9155

Search in Google Scholar

93 Coleman RS, Garg R. Org. Lett. 2001; 3: 3487

PubMed Search in Google Scholar

94 Santandrea J, Bédard A.-C, Collins SK. Org. Lett. 2014; 16: 3892

PubMed Search in Google Scholar

95 Piers E, Wong T. J. Org. Chem. 1993; 58: 3609

Search in Google Scholar

96 Paterson I, Lombart H.-G, Allerton C. Org. Lett. 1999; 1: 19

Search in Google Scholar

97 Tollefson EJ, Erickson LW, Jarvo ER. J. Am. Chem. Soc. 2015; 137: 9760

PubMed Search in Google Scholar

98 Durandetti M, Nédélec J.-Y, Périchon J. J. Org. Chem. 1996; 61: 1748

PubMed Search in Google Scholar

99 Durandetti M, Hardou L, Clément M, Maddaluno J. Chem. Commun. (Cambridge) 2009; 4753

PubMed

100 Everson DA, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920

PubMed Search in Google Scholar

101 Weix DJ. Acc. Chem. Res. 2015; 48: 1767

PubMed Search in Google Scholar

102 Li X, Feng Z, Jiang Z.-X, Zhang X. Org. Lett. 2015; 17: 5570

PubMed Search in Google Scholar

103 Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2015; 137: 10480

PubMed Search in Google Scholar

104 Cornella J, Edwards JT, Qin T, Kawamura S, Wang J, Pan C.-M, Gianatassio R, Schmidt M, Eastgate MD, Baran PS. J. Am. Chem. Soc. 2016; 138: 2174

PubMed Search in Google Scholar

105 Wang X, Wang S, Xue W, Gong H. J. Am. Chem. Soc. 2015; 137: 11562

PubMed Search in Google Scholar

106 Xue W, Xu H, Liang Z, Qian Q, Gong H. Org. Lett. 2014; 16: 4984

PubMed Search in Google Scholar

107 Yan C.-S, Peng Y, Xu X.-B, Wang Y.-W. Chem.–Eur. J. 2012; 18: 6039

Crossref PubMed Search in Google Scholar

108 Peng Y, Xu X.-B, Xiao J, Wang Y.-W. Chem. Commun. (Cambridge) 2014; 50: 472

PubMed Search in Google Scholar

109 Peng Y, Luo L, Yan C.-S, Zhang J.-J, Wang Y.-W. J. Org. Chem. 2013; 78: 10960

PubMed Search in Google Scholar