Cobalt-Catalyzed Alkynylation of Organic Compounds: Hydroalkynylation, Dehydrogenative Alkynylation, and Reductive Alkynylation

Yohei Ueda; Hayato Tsurugi; Kazushi Mashima

doi:10.1055/a-1983-2038

Synlett, Table of Contents

Synlett 2023; 34(09): 990-1000
DOI: 10.1055/a-1983-2038

account

Cobalt-Catalyzed Alkynylation of Organic Compounds: Hydroalkynylation, Dehydrogenative Alkynylation, and Reductive Alkynylation

Yohei Ueda

^aDepartment of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

,

Hayato Tsurugi ∗

^aDepartment of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

,

Kazushi Mashima∗

^bGraduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan

› Author Affiliations

Abstract

All articles of this category

Abstract

Cobalt-catalyzed hydroalkynylation of alkynes, alkenes, and imines affords internal alkynes with various functional groups adjacent to the carbon–carbon triple bond moiety in an atom-economical manner. In addition, cross-coupling of in situ generated alkynylcobalt species from terminal alkynes, haloalkynes, and metal acetylides with (hetero)aromatic compounds and organic halides selectively provides various internal aryl- and alkylalkynes.

1 Introduction

2 Hydroalkynylation of Alkynes for 1,3-Enyne Synthesis

3 Hydroalkynylation of Polar and Nonpolar Double Bonds

4 Dehydrogenative Cross-Coupling Reaction Using Terminal Alkynes with Aromatic Compounds

5 Cross-Coupling Reactions Using Haloalkynes as the Coupling Partners

6 Cross-Coupling Reactions Using Metal Acetylides

7 Conclusion

Key words

cobalt - alkynes - alkynylation - dimerization - haloalkynes - metal acetylides

Full Text

References

References

Representative books and reviews, see:

1a Acetylene Chemistry: Chemistry, Biology, and Material Science. Diederich F, Stang PJ, Tykwinski RR. VCH; Weinheim: 2005
1b Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations. Trost BM, Li C.-J. Wiley-VCH; Weinheim: 2015
1c Trotus IT, Zimmermann T, Schueth F. Chem. Rev. 2014; 114: 1761
1d Fürstner A, Davies PW. Angew. Chem. Int. Ed. 2007; 46: 3410
1e Hein JE, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
1f Gleiter R, Werz DB. Chem. Rev. 2010; 110: 4447
1g Godoi B, Schumacher RF, Zeni G. Chem. Rev. 2011; 111: 2937
1h Gilmore K, Alabugin IV. Chem. Rev. 2011; 111: 6513
1i Wille U. Chem. Rev. 2013; 113: 813
1j Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
1k Fang G, Bi X. Chem. Soc. Rev. 2015; 44: 8124

2 For a recent review, see: Shaw R, Elagamy A, Althagafi I, Pratap R. Org. Biomol. Chem. 2020; 18: 3797
3 Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 16: 4467

4a Chinchilla R, Najera C. Chem. Rev. 2007; 107: 874
4b Chinchilla R, Najera C. Chem. Soc. Rev. 2011; 40: 5084

5 Cobalt Catalysis in Organic Synthesis: Methods and Reactions. Lindsay DM, Kerr WJ. Wiley-VCH; Weinheim: 2020. and references therei

6a Trost BM, Masters JT. Chem. Soc. Rev. 2016; 45: 2212
6b Zhou Y, Zhang Y, Wang J. Org. Biomol. Chem. 2016; 14: 6638
6c Liang Q, Hayachi K, Song D. ACS Catal. 2020; 10: 4895

7 Vollhardt PC. Angew. Chem. Int. Ed. Engl. 1984; 23: 539
8 Hilt G, Hess W, Vogler T, Hengst C. J. Organomet. Chem. 2005; 690: 5170
9 Ventre S, Derat E, Amatore M, Aubert C, Petit M. Adv. Synth. Catal. 2013; 355: 2584
10 Zhuang X, Chen J.-Y, Yang Z, Jia M, Wu C, Liao R.-Z, Tung C.-H, Wang W. Organometallics 2019; 38: 3752
11 Hilt G, Weber SM, Queder J. Chem. Eur. J. 2020; 26: 12129
12 Xu D, Sun Q, Quan Z, Wang X, Sun W. Asian J. Org. Chem. 2018; 7: 155
13 Sakurada T, Sugiyama Y, Okamoto S. J. Org. Chem. 2013; 78: 3583
14 Grenier-Petel J, Collins SK. ACS Catal. 2019; 9: 3213
15 Ueda Y, Tsurugi H, Mashima K. Angew. Chem. Int. Ed. 2020; 59: 1552
16 Chen J.-F, Li C. ACS Catal. 2020; 10: 3881
17 Chen W, Bi H, Li C. Synlett 2010; 475
18 Chen J, Li C. Org. Lett. 2020; 22: 4686
19 Nishimura T, Sawano T, Ou K, Hayashi T. Chem. Commun. 2011; 47: 10142
20 Sawano T, Ashouri A, Nishimura T, Hayashi T. J. Am. Chem. Soc. 2012; 134: 18936
21 Sawano T, Ou K, Nishimura T, Hayashi T. Chem. Commun. 2012; 48: 6106
22 Sawano T, Ou K, Nishimura T, Hayashi T. J. Org. Chem. 2013; 78: 8986
23 Biletskyi B, Kong L, Tenaglia A, Clavier H. Adv. Synth. Catal. 2021; 363: 2578
24 Zhang L, Hao X, Liu Z, Zheng X, Zhang S, Niu J, Song M. Angew. Chem. Int. Ed. 2015; 54: 10012
25 Sauermann N, Gonzalez MJ, Ackermann L. Org. Lett. 2015; 17: 5316
26 Zhang Z, Liu B, Wang C, Shi B. Org. Lett. 2015; 17: 4094
27 Landge VG, Jaiswal G, Balaraman E. Org. Lett. 2016; 18: 812
28 Landge VG, Midya SP, Rana J, Shinde DR, Balaraman E. Org. Lett. 2016; 18: 5252
29 Mandal R, Barsu N, Garai B, Das A, Perekalin D, Sundararaju B. Chem. Commun. 2021; 57: 12167
30 Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2006; 8: 3093
31 Kuno A, Saino N, Kamachi T, Okamoto S. Tetrahedron Lett. 2006; 47: 2591
32 Hammann JM, Haas D, Tullmann C, Karaghiosoff K, Knochel P. Org. Lett. 2016; 18: 4778
33 Shirakawa E, Sato T, Imazaki Y, Kimura T, Hayashi T. Chem. Commun. 2007; 4513
34 Thomas L, Lutter FH, Hofmayer MS, Karaghiosoff K, Knochel P. Org. Lett. 2018; 20: 2441
35 Liu X, Zhou C, Lin E, Han X, Zhang S, Li Q, Wang H. Angew. Chem. Int. Ed. 2018; 57: 13096