Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence

Masahiko Shimada; Tatsuro Harumashi; Tomoya Miura; Masahiro Murakami

doi:10.1002/asia.200700407

Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence

Masahiko Shimada, Tatsuro Harumashi, Tomoya Miura, Masahiro Murakami

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

12 Citations (Scopus)

Abstract

Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I)complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, β-hydride elimination, hydro-rhodation, and β-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the β-hydride elimination/hydrorhodation process is repeatedly taking place.

Original language	English
Pages (from-to)	1035-1040
Number of pages	6
Journal	Chemistry - An Asian Journal
Volume	3
Issue number	6
DOIs	https://doi.org/10.1002/asia.200700407
Publication status	Published - Jun 2 2008
Externally published	Yes

Keywords

Boron
Catalysis
Cyclization
Elimination
Rhodium

ASJC Scopus subject areas

Chemistry(all)
Biochemistry
Organic Chemistry

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10.1002/asia.200700407

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abstract = "Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I)complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, β-hydride elimination, hydro-rhodation, and β-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the β-hydride elimination/hydrorhodation process is repeatedly taking place.",

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author = "Masahiko Shimada and Tatsuro Harumashi and Tomoya Miura and Masahiro Murakami",

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T1 - Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence

AU - Shimada, Masahiko

AU - Harumashi, Tatsuro

AU - Miura, Tomoya

AU - Murakami, Masahiro

PY - 2008/6/2

Y1 - 2008/6/2

N2 - Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I)complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, β-hydride elimination, hydro-rhodation, and β-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the β-hydride elimination/hydrorhodation process is repeatedly taking place.

AB - Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I)complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, β-hydride elimination, hydro-rhodation, and β-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the β-hydride elimination/hydrorhodation process is repeatedly taking place.

KW - Boron

KW - Catalysis

KW - Cyclization

KW - Elimination

KW - Rhodium

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Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence

Abstract

Keywords

ASJC Scopus subject areas

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