Photocatalytic Metal Hydride Hydrogen Atom Transfer Mediated Allene Functionalization by Cobalt and Titanium Dual Catalysis

Author:

Yan Huaipu1,Liao Qian1,Chen Yuqing1,Gurzadyan Gagik G.2ORCID,Lu Binghui3,Wu Chao4,Shi Lei13ORCID

Affiliation:

1. State Key Laboratory of Fine Chemicals School of Chemistry Dalian University of Technology Dalian 116024 China

2. State Key Laboratory of Fine Chemicals Institute of Artificial Photosynthesis Dalian University of Technology Dalian 116024 China

3. School of Chemistry and Chemical Engineering Henan Normal University Xinxiang, 2 453007 China

4. Frontier Institute of Science and Technology Xi'an Jiaotong University Xi An Shi, Xi'an 710054 China

Abstract

AbstractCatalytic metal hydride hydrogen atom transfer (MHAT) reactions have proven to be a powerful method for alkene functionalization. This work reports the discovery of Co‐porphines as highly efficient MHAT catalysts with a loading of only 0.01 mol % for unprecedented chemoselective allene functionalization under photoirradiation. Moreover, the newly developed bimetallic strategy by the combination of photo Co‐MHAT and Ti catalysis enabled the successful carbonyl allylation with a wide range of amino, oxy, thio, aryl, and alkyl‐allenes providing expedient access to valuable β‐functionalized homoallylic alcohols in over 100 examples with exceptional regio‐ and diastereoselectivity. Mechanism studies and DFT calculations supported that selectively transferring hydrogen atoms from cobalt hydride to allenes and generating allyl radicals is the key step in the catalytic cycle.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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