O–H Hydrogen bonding promotes H-atom transfer from α C–H bonds for C-alkylation of alcohols

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Science  27 Aug 2015:
DOI: 10.1126/science.aac8555

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The efficiency and selectivity of hydrogen atom transfer from organic molecules is often difficult to control in the presence of multiple potential hydrogen atom donors and acceptors. Herein, we describe the mechanistic evaluation of a mode of catalytic activation that accomplishes the highly selective photoredox α-alkylation/lactonization of alcohols with methyl acrylate via a hydrogen atom transfer mechanism. Our studies indicate a unique role of tetra-n-butylammonium phosphate in enhancing the selectivity for α C–H bonds in alcohols in the presence of allylic, benzylic, α-C=O, and α-ether C–H bonds.

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