Enhanced Excited-State Hydricity of Pd-H Allows for Unusual Head-to-Tail Hydroalkenylation of Alkenes

Sumon Sarkar; Soumen Ghosh; Daria Kurandina; Yusuf Noffel; Vladimir Gevorgyan

doi:10.1021/jacs.3c02410

Enhanced Excited-State Hydricity of Pd-H Allows for Unusual Head-to-Tail Hydroalkenylation of Alkenes

Sumon Sarkar, Soumen Ghosh, Daria Kurandina, Yusuf Noffel, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Photoinduced enhancement of hydricity of palladium hydride species enables unprecedented hydride addition-like ("hydridic") hydropalladation of electron-deficient alkenes, which allows for chemoselective head-to-tail cross-hydroalkenylation of electron-deficient and electron-rich alkenes. This mild and general protocol works with a wide range of densely functionalized and complex alkenes. Notably, this approach also allows for highly challenging cross-dimerization of electronically diverse vinyl arenes and heteroarenes.

Original language	English (US)
Pages (from-to)	12224-12232
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	145
Issue number	22
DOIs	https://doi.org/10.1021/jacs.3c02410
State	Published - Jun 7 2023
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.3c02410

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AU - Ghosh, Soumen

AU - Kurandina, Daria

AU - Noffel, Yusuf

AU - Gevorgyan, Vladimir

PY - 2023/6/7

Y1 - 2023/6/7

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AB - Photoinduced enhancement of hydricity of palladium hydride species enables unprecedented hydride addition-like ("hydridic") hydropalladation of electron-deficient alkenes, which allows for chemoselective head-to-tail cross-hydroalkenylation of electron-deficient and electron-rich alkenes. This mild and general protocol works with a wide range of densely functionalized and complex alkenes. Notably, this approach also allows for highly challenging cross-dimerization of electronically diverse vinyl arenes and heteroarenes.

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Enhanced Excited-State Hydricity of Pd-H Allows for Unusual Head-to-Tail Hydroalkenylation of Alkenes

Abstract

ASJC Scopus subject areas

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