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 2021; 53(11): 1889-1900
DOI: 10.1055/s-0040-1706024
DOI: 10.1055/s-0040-1706024
feature
Photocatalytic Generation of π-Allyltitanium Complexes from Butadiene via a Radical Strategy
The project was supported by Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University (No.2020YB03), National College Student Innovation and Entrepreneurship Training Program Support Project, Dalian University of Technology (No. 2020101410101010339), and LiaoNing Revitalization Talents Program (No. XLYC1907126).
Abstract
The direct conversion of industrial feedstock chemicals into highly valuable fine chemical intermediates is of great appeal to the synthetic community as well as industrial applications. This study reports a conceptually new radical strategy for the photocatalytic generation of π-allyltitanium complexes from butadiene. This novel and environmentally benign strategy enables the direct three-component allylation of carbonyls with 1,3-butadiene and α-bromocarboxylates, providing rapid access to valuable homoallylic alcohols with exceptional regio- and diastereoselectivity control.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706024.
- Supporting Information
Publication History
Received: 16 December 2020
Accepted after revision: 15 January 2021
Article published online:
18 February 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
- 2 Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2013; 113: 5595
- 3 Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
- 4 Knochel P, Dohle W, Gommermann N, Kneisel FF, Kopp F, Korn T, Sapountzis I, Vu VA. Angew. Chem. Int. Ed. 2003; 42: 4302
- 5 White WC. Chem. Biol. Interact. 2007; 166: 10
- 6 Grub J, Löser E. Butadiene . In Ullmann’s Encyclopedia of Industrial Chemistry, Vol. 6. Wiley-VCH; Weinheim: 2012: 381-396
- 7 Morrow NL. Environ. Health Perspect. 1990; 86: 7
- 8 Zbieg JR, Yamaguchi E, McInturff EL, Krische MJ. Science 2012; 336: 324
- 9 Holmes M, Schwartz LA, Krische MJ. Chem. Rev. 2018; 118: 6026
- 10a Takai K, Matsukawa N, Takahashi A, Fujii T. Angew. Chem. Int. Ed. 1998; 37: 152
- 10b Zhang G, Yang X. J. Am. Chem. Soc. 2018; 140: 2735
- 11 Li Y, Li W, Gu Z, Chen J, Xia J. ACS Catal. 2019; 10: 1528
- 12 Schwarz JL, Huang H, Paulisch TO, Glorius F. ACS Catal. 2019; 10: 1621
- 13 Boerth JA, Maity S, Williams SK, Mercado BQ, Ellman JA. Nat. Catal. 2018; 1: 673
- 14 Dongbang S, Shen Z, Ellman JA. Angew. Chem. Int. Ed. 2019; 58: 12590
- 15 Kimura M, Ezoe A, Mori M, Iwata K, Tamaru Y. J. Am. Chem. Soc. 2006; 128: 8559
- 16a Adamson NJ, Malcolmson SJ. ACS Catal. 2019; 10: 1060
- 16b Thullen SM, Rovis T. J. Am. Chem. Soc. 2017; 139: 15504
- 17 Huang HM, Bellotti P, Glorius F. Chem. Soc. Rev. 2020; 49: 6186
- 18 Huang H, Koy M, Serrano E, Pflüger PM, Schwarz JL, Glorius F. Nat. Catal. 2020; 3: 393
- 19 Huang H, Bellotti P, Pflüger PM, Schwarz JL, Heidrich B, Glorius F. J. Am. Chem. Soc. 2020; 142: 10173
- 20 Cheung KP. S, Kurandina D, Yata T, Gevorgyan V. J. Am. Chem. Soc. 2020; 142: 9932
- 21 Rosales A, Rodríguez-García I, Muñoz-Bascón J, Roldan-Molina E, Padial NM, Morales LP, García-Ocaña M, Oltra JE. Eur. J. Org. Chem. 2015; 4567
- 22 McCallum T, Wu X, Lin S. J. Org. Chem. 2019; 84: 14369
- 23 Twilton J, Le CC, Zhang P, Shaw MH, Evans RW, MacMillan DW. C. Nat. Rev. Chem. 2017; 1: 52
- 24 Tellis JC, Kelly CB, Primer DN, Jouffroy M, Patel NR, Molander GA. Acc. Chem. Res. 2016; 49: 1429
- 25 Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
- 26 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
- 27 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 28 Lin S, Chen Y, Li F, Shi C, Shi L. Chem. Sci. 2020; 11: 839
- 29a Li F, Chen Y, Lin S, Shi C, Li X, Sun Y, Guo Z, Shi L. Org. Chem. Front. 2020; 7: 3434
- 29b Li F, Lin S, Chen Y, Shi C, Yan H, Li C, Wu C, Lin L, Duan C, Shi L. Angew. Chem.Int. Ed. 2021; 60: 1561
- 29c Gualandi A, Calogero F, Mazzarini M, Guazzi S, Fermi A, Bergamini G, Cozzi PG. ACS Catal. 2020; 10: 3857
- 30 Chen Y, Lin S, Li F, Zhang X, Lin L, Shi L. ChemPhotoChem 2020; 4: 659
- 31 Nugent WA, RajanBabu TV. J. Am. Chem. Soc. 1988; 110: 8561