Unique effect of coordination of an alkene moiety in products on Ruthenium-catalyzed chemoselective C-H alkenylation

Satoshi Ueno; Takuya Kochi; Naoto Chatani; Fumitoshi Kakiuchi

doi:10.1021/ol802819b

Unique effect of coordination of an alkene moiety in products on Ruthenium-catalyzed chemoselective C-H alkenylation

Satoshi Ueno, Takuya Kochi, Naoto Chatani, Fumitoshi Kakiuchi

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

31 Citations (Scopus)

Abstract

Ruthenium-catalyzed alkenylation of 2'-alkoxyacetophenones with alkenylboronates provides ortho C-H alkenylation products without sacrificing an ether functional group at the other ortho position. Both excellent chemoselectivity and high product yields are achieved with an aryloxo ruthenium complex. The effective suppression of the C-O bond cleavage was attained by coordination of the alkenyl moiety in the C-H alkenylation product to the ruthenium center.

Original language	English
Pages (from-to)	855-858
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	4
DOIs	https://doi.org/10.1021/ol802819b
Publication status	Published - 2009 Feb 19
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802819b

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abstract = "Ruthenium-catalyzed alkenylation of 2'-alkoxyacetophenones with alkenylboronates provides ortho C-H alkenylation products without sacrificing an ether functional group at the other ortho position. Both excellent chemoselectivity and high product yields are achieved with an aryloxo ruthenium complex. The effective suppression of the C-O bond cleavage was attained by coordination of the alkenyl moiety in the C-H alkenylation product to the ruthenium center.",

author = "Satoshi Ueno and Takuya Kochi and Naoto Chatani and Fumitoshi Kakiuchi",

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T1 - Unique effect of coordination of an alkene moiety in products on Ruthenium-catalyzed chemoselective C-H alkenylation

AU - Ueno, Satoshi

AU - Kochi, Takuya

AU - Chatani, Naoto

AU - Kakiuchi, Fumitoshi

PY - 2009/2/19

Y1 - 2009/2/19

N2 - Ruthenium-catalyzed alkenylation of 2'-alkoxyacetophenones with alkenylboronates provides ortho C-H alkenylation products without sacrificing an ether functional group at the other ortho position. Both excellent chemoselectivity and high product yields are achieved with an aryloxo ruthenium complex. The effective suppression of the C-O bond cleavage was attained by coordination of the alkenyl moiety in the C-H alkenylation product to the ruthenium center.

AB - Ruthenium-catalyzed alkenylation of 2'-alkoxyacetophenones with alkenylboronates provides ortho C-H alkenylation products without sacrificing an ether functional group at the other ortho position. Both excellent chemoselectivity and high product yields are achieved with an aryloxo ruthenium complex. The effective suppression of the C-O bond cleavage was attained by coordination of the alkenyl moiety in the C-H alkenylation product to the ruthenium center.

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Unique effect of coordination of an alkene moiety in products on Ruthenium-catalyzed chemoselective C-H alkenylation

Abstract

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