The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates

Yusuke Matsuura; Masaru Tamura; Takuya Kochi; Mitsuo Sato; Naoto Chatani; Fumitoshi Kakiuchi

doi:10.1021/ja071965m

The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates

Yusuke Matsuura, Masaru Tamura, Takuya Kochi, Mitsuo Sato, Naoto Chatani, Fumitoshi Kakiuchi

Department of Chemistry

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

137 Citations (Scopus)

Abstract

The regioselective Ru(cod)(cot)-catalyzed alkenylation of arylpyridines and related compounds with alkenyl acetates to give good-to-excellent yields of ortho-alkenylation products was developed. Several arylpyridines having electron-donating (CH₃ and OCH₃) and -withdrawing (CF₃, CN, and Ac) groups and azoles, such as oxazoline, tetrazole, and thiazole, can be used in this coupling reaction. A variety of alkenyl acetates, such as 1-propenyl, 1-butenyl, 1-hexenyl, styryl, 2-methyl-1-propenyl, and 1-cyclohexenyl acetates, reacted with arylpyridines to give the corresponding ortho-alkenylation products in high yields. This direct alkenylation of aromatic C-H bonds with alkenyl acetates provides π-conjugated aromatic and heteroaromatic compounds under halogen-free reaction conditions.

Original language	English
Pages (from-to)	9858-9859
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	32
DOIs	https://doi.org/10.1021/ja071965m
Publication status	Published - 2007 Aug 15

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates",

abstract = "The regioselective Ru(cod)(cot)-catalyzed alkenylation of arylpyridines and related compounds with alkenyl acetates to give good-to-excellent yields of ortho-alkenylation products was developed. Several arylpyridines having electron-donating (CH3 and OCH3) and -withdrawing (CF3, CN, and Ac) groups and azoles, such as oxazoline, tetrazole, and thiazole, can be used in this coupling reaction. A variety of alkenyl acetates, such as 1-propenyl, 1-butenyl, 1-hexenyl, styryl, 2-methyl-1-propenyl, and 1-cyclohexenyl acetates, reacted with arylpyridines to give the corresponding ortho-alkenylation products in high yields. This direct alkenylation of aromatic C-H bonds with alkenyl acetates provides π-conjugated aromatic and heteroaromatic compounds under halogen-free reaction conditions.",

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AU - Matsuura, Yusuke

AU - Tamura, Masaru

AU - Kochi, Takuya

AU - Sato, Mitsuo

AU - Chatani, Naoto

AU - Kakiuchi, Fumitoshi

PY - 2007/8/15

Y1 - 2007/8/15

N2 - The regioselective Ru(cod)(cot)-catalyzed alkenylation of arylpyridines and related compounds with alkenyl acetates to give good-to-excellent yields of ortho-alkenylation products was developed. Several arylpyridines having electron-donating (CH3 and OCH3) and -withdrawing (CF3, CN, and Ac) groups and azoles, such as oxazoline, tetrazole, and thiazole, can be used in this coupling reaction. A variety of alkenyl acetates, such as 1-propenyl, 1-butenyl, 1-hexenyl, styryl, 2-methyl-1-propenyl, and 1-cyclohexenyl acetates, reacted with arylpyridines to give the corresponding ortho-alkenylation products in high yields. This direct alkenylation of aromatic C-H bonds with alkenyl acetates provides π-conjugated aromatic and heteroaromatic compounds under halogen-free reaction conditions.

AB - The regioselective Ru(cod)(cot)-catalyzed alkenylation of arylpyridines and related compounds with alkenyl acetates to give good-to-excellent yields of ortho-alkenylation products was developed. Several arylpyridines having electron-donating (CH3 and OCH3) and -withdrawing (CF3, CN, and Ac) groups and azoles, such as oxazoline, tetrazole, and thiazole, can be used in this coupling reaction. A variety of alkenyl acetates, such as 1-propenyl, 1-butenyl, 1-hexenyl, styryl, 2-methyl-1-propenyl, and 1-cyclohexenyl acetates, reacted with arylpyridines to give the corresponding ortho-alkenylation products in high yields. This direct alkenylation of aromatic C-H bonds with alkenyl acetates provides π-conjugated aromatic and heteroaromatic compounds under halogen-free reaction conditions.

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The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates

Abstract

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