Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp 2 and sp3 boronic acids using air as the oxidant

Dong Hui Wang; Masayuki Wasa; Ramesh Giri; Jin Quan Yu

doi:10.1021/ja801355s

Pd(II)-catalyzed cross-coupling of sp³ C-H bonds with sp ² and sp³ boronic acids using air as the oxidant

Dong Hui Wang, Masayuki Wasa, Ramesh Giri, Jin Quan Yu

Chemistry

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

446 Scopus citations

Abstract

O-Methyl hydroxamic acids, readily available from carboxylic acids, are found to be extremely reactive for β-C-H activation by Pd(OAc)₂. This reactivity is exploited to develop the first example of cross-coupling sp³ C-H bonds with sp³ boronic acids. Air was shown to be a suitable stoichiometric oxidant for the catalytic oxidative coupling reaction. A biologically active natural product is readily converted to its novel analogues through this coupling reaction.

Original language	English (US)
Pages (from-to)	7190-7191
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	23
DOIs	https://doi.org/10.1021/ja801355s
State	Published - Jun 11 2008

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja801355s

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abstract = "O-Methyl hydroxamic acids, readily available from carboxylic acids, are found to be extremely reactive for β-C-H activation by Pd(OAc)2. This reactivity is exploited to develop the first example of cross-coupling sp3 C-H bonds with sp3 boronic acids. Air was shown to be a suitable stoichiometric oxidant for the catalytic oxidative coupling reaction. A biologically active natural product is readily converted to its novel analogues through this coupling reaction.",

author = "Wang, {Dong Hui} and Masayuki Wasa and Ramesh Giri and Yu, {Jin Quan}",

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AU - Giri, Ramesh

AU - Yu, Jin Quan

PY - 2008/6/11

Y1 - 2008/6/11

N2 - O-Methyl hydroxamic acids, readily available from carboxylic acids, are found to be extremely reactive for β-C-H activation by Pd(OAc)2. This reactivity is exploited to develop the first example of cross-coupling sp3 C-H bonds with sp3 boronic acids. Air was shown to be a suitable stoichiometric oxidant for the catalytic oxidative coupling reaction. A biologically active natural product is readily converted to its novel analogues through this coupling reaction.

AB - O-Methyl hydroxamic acids, readily available from carboxylic acids, are found to be extremely reactive for β-C-H activation by Pd(OAc)2. This reactivity is exploited to develop the first example of cross-coupling sp3 C-H bonds with sp3 boronic acids. Air was shown to be a suitable stoichiometric oxidant for the catalytic oxidative coupling reaction. A biologically active natural product is readily converted to its novel analogues through this coupling reaction.

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Pd(II)-catalyzed cross-coupling of sp³ C-H bonds with sp ² and sp³ boronic acids using air as the oxidant

Abstract

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