Development of highly efficient platinum catalysts for hydroalkoxylation and hydroamination of unactivated alkenes

Yali Zhou, Xingjun Xu, Hongwei Sun, Guanyu Tao, Xiao-Yong Chang, Xiangyou Xing (), Bo Chen () and Chen Xu ()
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Yali Zhou: Southern University of Science and Technology
Xingjun Xu: Southern University of Science and Technology
Hongwei Sun: Southern University of Science and Technology
Guanyu Tao: Southern University of Science and Technology
Xiao-Yong Chang: Southern University of Science and Technology
Xiangyou Xing: Southern University of Science and Technology
Bo Chen: Southern University of Science and Technology
Chen Xu: Southern University of Science and Technology

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Hydrofunctionalization, the direct addition of an X–H (e.g., X=O, N) bond across an alkene, is a desirable strategy to make heterocycles that are important structural components of naturally occurring molecules. Described here is the design and discovery of “donor–acceptor”-type platinum catalysts that are highly effective in both hydroalkoxylation and hydroamination of unactivated alkenes over a broad range of substrates under mild conditions. A number of alkene substitution patterns are accommodated, including tri-substituted, 1,1-disubstituted, (E)-disubstituted, (Z)-disubstituted and even mono-substituted double bonds. Detailed mechanistic investigations suggest a plausible pathway that includes an unexpected dissociation/re-association of the electron-deficient ligand to form an alkene-bound “donor–acceptor”-type intermediate. These mechanistic studies help understand the origins of the high reactivity exhibited by the catalytic system, and provide a foundation for the rational design of chiral catalysts towards asymmetric hydrofunctionalization reactions.

Date: 2021
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DOI: 10.1038/s41467-021-22287-w

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