Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2020; 52(04): 529-536
DOI: 10.1055/s-0039-1690014
DOI: 10.1055/s-0039-1690014
paper
Allylic C–H Alkynylation via Copper-Photocatalyzed Cross-Dehydrogenative Coupling
Financial support by the German Academic Exchange Service, DAAD (Leadership for Syria Program) is gratefully acknowledged.Further Information
Publication History
Received: 30 April 2019
Accepted after revision: 18 July 2019
Publication Date:
25 July 2019 (online)
Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry
Abstract
An efficient, novel photocatalyzed allylic-alkynylation methodology via copper-based cross-dehydrogenative coupling (CDC) is described. Different types of 1,4-enyne compounds were synthesized in one step at room temperature using copper(I) terpyridyl complex as photocatalyst/initiator. This procedure is an improvement and to some extent complementary to previously reported thermal CDC methods. Preliminary investigations on the reaction mechanism are also presented.
Key words
C–C bond - copper catalyst - C–H functionalization - photocatalyst - allylic-alkynylation - 1,4-enyneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690014.
- Supporting Information
-
References
- 1a Whang DR, Apaydin DH. ChemPhotoChem 2018; 2: 148
- 1b Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 52
- 1c Marzo L, Pagire SK, Reiser O, Konig B. Angew. Chem. Int. Ed. 2018; 57: 10034
- 2 Trost BM, Crawley ML. Top. Organomet. Chem. 2012; 38: 321
- 3 Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem. Eur. J. 2012; 18: 7336
- 4a Knorn M, Rawner T, Czerwieniec R, Reiser O. ACS Catal. 2015; 5: 5186
- 4b Reiser O. Acc. Chem. Res. 2016; 49: 1990
- 5 Baralle A, Fensterbank L, Goddard J.-P, Ollivier C. Chem. Eur. J. 2013; 19: 10809
-
6
Cuthbertson JD,
MacMillan DW. C.
Nature 2015; 519 (7541): 74
- 7 Almasalma AA, Mejia E. Chem. Eur. J. 2018; 24: 12269
- 8 Tsang AS.-K, Park SJ, Todd MH. In From C-H to C-C Bonds: Cross-Dehydrogenative-Coupling, RSC Green Chemistry Vol. 26. Li C.-J. The Royal Society of Chemistry; Cambridge: 2015: 254-294
- 9a Li C.-J. Acc. Chem. Res. 2009; 42: 335
- 9b Girard SA, Knauber T, Li CJ. Angew. Chem. Int. Ed. 2014; 53: 74
- 9c Li Z, Li CJ. J. Am. Chem. Soc. 2006; 128: 56
- 9d Varun BV, Dhineshkumar J, Bettadapur KR, Siddaraju Y, Alagiri K, Prabhu KR. Tetrahedron Lett. 2017; 58: 803
- 9e Yoo W.-J, Li C.-J. C-H Activation. In Topics in Current Chemistry, Vol. 292. Yu J.-Q, Shi Z. Springer; Berlin: 2010: 281-302
- 9f Zheng X, Li Z. In From C-H to C-C Bonds: Cross-Dehydrogenative-Coupling, RSC Green Chemistry Vol. 26. Li C.-J. The Royal Society of Chemistry; Cambridge: 2015: 55-66
- 10 Chen B, Wu LZ, Tung CH. Acc. Chem. Res. 2018; 51: 2512
- 11 Constable EC. Chem. Soc. Rev. 2007; 36: 246
- 12 Harriman A, Ziessel R. Coord. Chem. Rev. 1998; 171: 331
- 13 Heller M, Schubert US. Eur. J. Org. Chem. 2003; 947
- 14a Yan X, Zhang J. Chem. Res. Chin. Univ. 2017; 33: 1
- 14b Huang J.-B, Bai X.-F, Li L, Zheng Z.-J, Xu Z, Cui Y.-M, Cao J, Xu L.-W. Chem. Eur. J. 2017; 23: 4055
- 15a Rajalakshmi S, Weyhermüller T, Dinesh M, Nair BU. J. Inorg. Biochem. 2012; 117: 48
- 15b Zhang Y, Schulz M, Wächtler M, Karnahl M, Dietzek B. Coord. Chem. Rev. 2018; 356: 127
- 15c Hogg R, Wilkins RG. J. Chem. Soc. 1962; 341
- 16a Potts KT, Keshavarz-K M, Tham FS, Raiford KA. G, Arana C, Abruna HD. Inorg. Chem. 1993; 32: 5477
- 16b Potts KT, Keshavarz-K M, Tham FS, Abruna HD, Arana CR. Inorg. Chem. 1993; 32: 4422
- 16c Munakata M, Nishibayashi S, Sakamoto H. J. Chem. Soc., Chem. Commun. 1980; 219
- 16d Crumbliss AL, Poulos AT. Inorg. Chem. 1975; 14: 1529
- 17 Pflaum RT, Brandt WW. J. Am. Chem. Soc. 1955; 77: 2019
- 18 Sagadevan A, Hwang KC. Adv. Synth. Catal. 2012; 354: 3421
- 19 Wu JJ, Li YW, Zhou HY, Wen AH, Lun CC, Yao SY, Ke ZF, Ye BH. ACS Catal. 2016; 6: 1263
- 20 Li J, Zhang J, Tan H, Wang DZ. Org. Lett. 2015; 17: 2522
- 21 Ogino K, Kanegae A, Yamaguchi R, Sato H, Kurjata J. Macromol. Rapid Commun. 1999; 20: 103
- 22 Photosensitive Metal – Organic Systems. Kutal C, Serpone N. In Advances in Chemistry. Vol 238 American Chemical Society; Washington: 1993
- 23 Manbeck GF, Brennessel WW, Eisenberg R. Inorg. Chem. 2011; 50: 3431
- 24a Chow YL, Buono-Core GE. J. Am. Chem. Soc. 1986; 108: 1234
- 24b Beckwith AL. J, Zavitsas AA. J. Am. Chem. Soc. 1986; 108: 8230
- 25 Casitas A, Ribas X. Chem. Sci. 2013; 4: 2301
- 26 Li Z, Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810
- 27a Huang JB, Bai XF, Li L, Zheng ZJ, Xu Z, Cui YM, Cao J, Xu LW. Chem. Eur. J. 2017; 23: 4055
- 27b Xiao P, Dumur F, Zhang J, Fouassier JP, Gigmes D, Lalevée J. Macromolecules 2014; 47: 3837
- 28 Rayabarapu DK, Tunge JA. J. Am. Chem. Soc. 2005; 127: 13510