Journal
CHEMICAL SOCIETY REVIEWS
Volume 50, Issue 5, Pages 3263-3314Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cs00447b
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Funding
- National Natural Science Foundation of China (NSFC) [21672048]
- Natural Science Foundation of Zhejiang Province (ZJNSF) [LY19B020006]
- Hangzhou Normal University
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The article discusses the current status and challenges of olefinic C-H functionalization, emphasizing recent significant advances in this field, especially geminal-group-directed C-H functionalization and distal-selective alkenyl C-H functionalization.
Olefinic C-H functionalization represents an atom- and step economic approach to valuable olefin derivatives from simpler ones, but controlling the selectivity remains a challenge. Remarkable progress has been made in the site-selective C-H functionalization of arenes and alkanes, but there are still limited examples of selective C-H functionalization of olefins presumably due to the lability and easy decomposition of the alkenyl moiety. Chelation-assisted C-H activation represents an efficient protocol for site- and stereo-selective construction of carbon-carbon and carbon-heteroatom bonds. This review highlights recent advances in vicinal- and geminal-group-directed olefinic C-H functionalization, including alkenylation, arylation, alkynylation, alkylation, halogenation, silylation, cyanation and annulation by the formation of exo-/endo-metallocycles. In particular, geminal-group-directed C-H functionalization is covered for the first time, as well as distal-selective alkenyl C-H functionalization under palladium/norbornene cooperative catalysis, which provides novel disconnections in retrosynthetic analysis and represents the future trend in green chemistry.
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