Control of product selectivity by a styrene additive in ruthenium-catalyzed C-H arylation

Shun Hiroshima; Daiki Matsumura; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/ol102325f

Control of product selectivity by a styrene additive in ruthenium-catalyzed C-H arylation

Shun Hiroshima, Daiki Matsumura, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

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

37 Citations (Scopus)

Abstract

A unique effect of styrene additive on product selectivity was observed for RuH₂(CO)(PPh₃)₃-catalyzed C-H arylation of acetophenone derivatives bearing two ortho C-H bonds. Without styrene, the C-H arylation with arylboronates gives diarylation products as the major products throughout the reaction, but the use of styrene as an additive switches the product selectivity and leads to selective formation of monoarylation products.

Original language	English
Pages (from-to)	5318-5321
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	22
DOIs	https://doi.org/10.1021/ol102325f
Publication status	Published - 2010 Nov 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102325f

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abstract = "A unique effect of styrene additive on product selectivity was observed for RuH2(CO)(PPh3)3-catalyzed C-H arylation of acetophenone derivatives bearing two ortho C-H bonds. Without styrene, the C-H arylation with arylboronates gives diarylation products as the major products throughout the reaction, but the use of styrene as an additive switches the product selectivity and leads to selective formation of monoarylation products.",

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AU - Hiroshima, Shun

AU - Matsumura, Daiki

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2010/11/19

Y1 - 2010/11/19

N2 - A unique effect of styrene additive on product selectivity was observed for RuH2(CO)(PPh3)3-catalyzed C-H arylation of acetophenone derivatives bearing two ortho C-H bonds. Without styrene, the C-H arylation with arylboronates gives diarylation products as the major products throughout the reaction, but the use of styrene as an additive switches the product selectivity and leads to selective formation of monoarylation products.

AB - A unique effect of styrene additive on product selectivity was observed for RuH2(CO)(PPh3)3-catalyzed C-H arylation of acetophenone derivatives bearing two ortho C-H bonds. Without styrene, the C-H arylation with arylboronates gives diarylation products as the major products throughout the reaction, but the use of styrene as an additive switches the product selectivity and leads to selective formation of monoarylation products.

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Control of product selectivity by a styrene additive in ruthenium-catalyzed C-H arylation

Abstract

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