Rh-catalyzed carbonylation of arylzinc compounds yielding symmetrical diaryl ketones by the assistance of oxidizing agents

Kana Kobayashi; Yugo Nishimura; Fuxing Gao; Kazuma Gotoh; Yasushi Nishihara; Kentaro Takagi

doi:10.1021/jo1025173

Rh-catalyzed carbonylation of arylzinc compounds yielding symmetrical diaryl ketones by the assistance of oxidizing agents

Kana Kobayashi, Yugo Nishimura, Fuxing Gao, Kazuma Gotoh, Yasushi Nishihara, Kentaro Takagi

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

31 Citations (Scopus)

Abstract

Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh-dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts induced oxidative homocoupling of 1 to yield biaryls instead. The beneficial catalysis by Rh in the carbonylation was presumed to stem from the facility by which the migration of the aryl ligand to CO at the Rh³⁺ intermediate occurred.

Original language	English
Pages (from-to)	1949-1952
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	76
Issue number	6
DOIs	https://doi.org/10.1021/jo1025173
Publication status	Published - Mar 18 2011

ASJC Scopus subject areas

Organic Chemistry

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abstract = "Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh-dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts induced oxidative homocoupling of 1 to yield biaryls instead. The beneficial catalysis by Rh in the carbonylation was presumed to stem from the facility by which the migration of the aryl ligand to CO at the Rh3+ intermediate occurred.",

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T1 - Rh-catalyzed carbonylation of arylzinc compounds yielding symmetrical diaryl ketones by the assistance of oxidizing agents

AU - Kobayashi, Kana

AU - Nishimura, Yugo

AU - Gao, Fuxing

AU - Gotoh, Kazuma

AU - Nishihara, Yasushi

AU - Takagi, Kentaro

PY - 2011/3/18

Y1 - 2011/3/18

N2 - Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh-dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts induced oxidative homocoupling of 1 to yield biaryls instead. The beneficial catalysis by Rh in the carbonylation was presumed to stem from the facility by which the migration of the aryl ligand to CO at the Rh3+ intermediate occurred.

AB - Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh-dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts induced oxidative homocoupling of 1 to yield biaryls instead. The beneficial catalysis by Rh in the carbonylation was presumed to stem from the facility by which the migration of the aryl ligand to CO at the Rh3+ intermediate occurred.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

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Rh-catalyzed carbonylation of arylzinc compounds yielding symmetrical diaryl ketones by the assistance of oxidizing agents

Abstract

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