4.8 Review

Direct Sp(3) alpha-C-H activation and functionalization of alcohol and ether

Journal

CHEMICAL SOCIETY REVIEWS
Volume 40, Issue 4, Pages 1937-1949

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0cs00063a

Keywords

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Funding

  1. NSFC [20732002, 20921120404, 20972059, 21072085]
  2. MOE
  3. MOST [2010CB833203]

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Seven kinds of sp(3) alpha-C-H activation/C-C formation reactions of alcohols and ethers have been reviewed in this tutorial review, from the viewpoint of both methodology and synthetic application, towards the efficiency, chemo-, regio- and stereoselectivity, catalytic system, substrate scope and mechanistic study. Section 2 describes radical-mediated alpha-C-H activation and addition/elimination of ethers with unsaturated (C=C and C C) species. Sections 3-8 discuss the alpha-C-H activation and additions of alcohols and/or ethers with unsaturated (C=C, C C, C=O and C=N) compounds, which involve the key processes of radical mediation, carbenoid insertion, 1,5-H-migration, oxidative dehydrogenation coupling, transfer hydrogenative coupling, and metal-mediated C=C insertion into the C-H bond.

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