Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis

Yuto Hashimoto; Koji Hirano; Tetsuya Satoh; Fumitoshi Kakiuchi; Masahiro Miura

doi:10.1021/jo3025237

Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis

Yuto Hashimoto, Koji Hirano, Tetsuya Satoh, Fumitoshi Kakiuchi, Masahiro Miura

Department of Chemistry

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

73 Citations (Scopus)

Abstract

The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.

Original language	English
Pages (from-to)	638-646
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	78
Issue number	2
DOIs	https://doi.org/10.1021/jo3025237
Publication status	Published - 2013 Jan 18

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo3025237

Cite this

@article{8b6cab24a1e74e56b548577ea78873b7,

title = "Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis",

abstract = "The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.",

author = "Yuto Hashimoto and Koji Hirano and Tetsuya Satoh and Fumitoshi Kakiuchi and Masahiro Miura",

year = "2013",

month = jan,

day = "18",

doi = "10.1021/jo3025237",

language = "English",

volume = "78",

pages = "638--646",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis

AU - Hashimoto, Yuto

AU - Hirano, Koji

AU - Satoh, Tetsuya

AU - Kakiuchi, Fumitoshi

AU - Miura, Masahiro

PY - 2013/1/18

Y1 - 2013/1/18

N2 - The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.

AB - The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.

UR - http://www.scopus.com/inward/record.url?scp=84872564556&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84872564556&partnerID=8YFLogxK

U2 - 10.1021/jo3025237

DO - 10.1021/jo3025237

M3 - Article

C2 - 23237055

AN - SCOPUS:84872564556

SN - 0022-3263

VL - 78

SP - 638

EP - 646

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Regioselective C-H bond cleavage/alkyne insertion under ruthenium catalysis

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this