Palladium-catalyzed regioselective homocoupling of arenes using anodic oxidation: Formal electrolysis of aromatic carbon-hydrogen bonds

Fumito Saito; Hiroko Aiso; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/om500957a

Palladium-catalyzed regioselective homocoupling of arenes using anodic oxidation: Formal electrolysis of aromatic carbon-hydrogen bonds

Fumito Saito, Hiroko Aiso, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

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

79 Citations (Scopus)

Abstract

Palladium-catalyzed regioselective homocoupling of arylpyridines under anodic oxidation conditions was achieved in the presence of I₂. The dimerization of meta-substituted arylpyridines proceeded selectively at less-sterically congested ortho-positions, and the selectivity is different from that reported for the palladium-catalyzed dimerization using Oxone as an oxidant. The dimerization also proceeds using catalytic amounts of both Pd(OAc)₂ and I₂ under the electrochemical reaction conditions.

Original language	English
Pages (from-to)	6704-6707
Number of pages	4
Journal	Organometallics
Volume	33
Issue number	22
DOIs	https://doi.org/10.1021/om500957a
Publication status	Published - 2014 Nov 24

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "Palladium-catalyzed regioselective homocoupling of arylpyridines under anodic oxidation conditions was achieved in the presence of I2. The dimerization of meta-substituted arylpyridines proceeded selectively at less-sterically congested ortho-positions, and the selectivity is different from that reported for the palladium-catalyzed dimerization using Oxone as an oxidant. The dimerization also proceeds using catalytic amounts of both Pd(OAc)2 and I2 under the electrochemical reaction conditions.",

author = "Fumito Saito and Hiroko Aiso and Takuya Kochi and Fumitoshi Kakiuchi",

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T1 - Palladium-catalyzed regioselective homocoupling of arenes using anodic oxidation

T2 - Formal electrolysis of aromatic carbon-hydrogen bonds

AU - Saito, Fumito

AU - Aiso, Hiroko

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2014/11/24

Y1 - 2014/11/24

N2 - Palladium-catalyzed regioselective homocoupling of arylpyridines under anodic oxidation conditions was achieved in the presence of I2. The dimerization of meta-substituted arylpyridines proceeded selectively at less-sterically congested ortho-positions, and the selectivity is different from that reported for the palladium-catalyzed dimerization using Oxone as an oxidant. The dimerization also proceeds using catalytic amounts of both Pd(OAc)2 and I2 under the electrochemical reaction conditions.

AB - Palladium-catalyzed regioselective homocoupling of arylpyridines under anodic oxidation conditions was achieved in the presence of I2. The dimerization of meta-substituted arylpyridines proceeded selectively at less-sterically congested ortho-positions, and the selectivity is different from that reported for the palladium-catalyzed dimerization using Oxone as an oxidant. The dimerization also proceeds using catalytic amounts of both Pd(OAc)2 and I2 under the electrochemical reaction conditions.

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Palladium-catalyzed regioselective homocoupling of arenes using anodic oxidation: Formal electrolysis of aromatic carbon-hydrogen bonds

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