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Chen SY, Li Q, Wang H. Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes. J Org Chem. 2017;82(20):11173-11181doi: 10.1021/acs.joc.7b02220.
Chen, S. Y., Li, Q., & Wang, H. (2017). Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes. The Journal of organic chemistry, 82(20), 11173-11181. https://doi.org/10.1021/acs.joc.7b02220
Chen, Shi-Yong, et al. "Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes." The Journal of organic chemistry vol. 82,20 (2017): 11173-11181. doi: https://doi.org/10.1021/acs.joc.7b02220
Chen SY, Li Q, Wang H. Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes. J Org Chem. 2017 Oct 20;82(20):11173-11181. doi: 10.1021/acs.joc.7b02220. Epub 2017 Oct 03. PMID: 28948781.
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J Org Chem. 2017 Oct 20;82(20):11173-11181. doi: 10.1021/acs.joc.7b02220. Epub 2017 Oct 03.

Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes.

The Journal of organic chemistry

Shi-Yong Chen, Qingjiang Li, Honggen Wang

Affiliations

  1. School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, 510006, China.
  2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University , Beijing, 100191, China.

PMID: 28948781 DOI: 10.1021/acs.joc.7b02220

Abstract

Polysubstituted allyl groups, for example, the prenyl group, are valuable synthetic handles and widely encountered in bioactive compounds. Reported herein is a manganese(I)-catalyzed direct C-H coupling with allenes for the efficient assembly of allylated arenes. The protocol offers an extremely high level of atom-economy and is particularly suited for the introduction of 1,1-disubstitiuted allyl groups, as exemplified by the quantitative syntheses of a variety of prenylated indoles. The practicality of this method was evidenced by a gram-scale synthesis with a lower catalyst loading of manganese(I) (2.5 mol %, 95% yield). Experimental mechanistic studies were conducted, and a possible reaction mechanism was proposed.

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