Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement

Mieko Arisawa; Manabu Kuwajima; Fumihiko Toriyama; Guangzhe Li; Masahiko Yamaguchi

doi:10.1021/ol3017148

Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement

Mieko Arisawa, Manabu Kuwajima, Fumihiko Toriyama, Guangzhe Li, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

41 Citations (Scopus)

Abstract

In the presence of catalytic amounts of RhH(CO)(PPh₃) ₃ and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO-C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chlorophenyl)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.

Original language	English
Pages (from-to)	3804-3807
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	14
DOIs	https://doi.org/10.1021/ol3017148
Publication status	Published - 2012 Jul 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3017148

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title = "Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement",

abstract = "In the presence of catalytic amounts of RhH(CO)(PPh3) 3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO-C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chlorophenyl)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.",

author = "Mieko Arisawa and Manabu Kuwajima and Fumihiko Toriyama and Guangzhe Li and Masahiko Yamaguchi",

year = "2012",

month = jul,

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doi = "10.1021/ol3017148",

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journal = "Organic Letters",

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T1 - Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters

T2 - Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement

AU - Arisawa, Mieko

AU - Kuwajima, Manabu

AU - Toriyama, Fumihiko

AU - Li, Guangzhe

AU - Yamaguchi, Masahiko

PY - 2012/7/20

Y1 - 2012/7/20

N2 - In the presence of catalytic amounts of RhH(CO)(PPh3) 3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO-C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chlorophenyl)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.

AB - In the presence of catalytic amounts of RhH(CO)(PPh3) 3 and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO-C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chlorophenyl)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.

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SN - 1523-7060

VL - 14

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JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Rhodium-catalyzed acyl-transfer reaction between benzyl ketones and thioesters: Synthesis of unsymmetric ketones by ketone CO-C bond cleavage and intermolecular rearrangement

Abstract

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