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

30 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

Access to Document

10.1021/ol802819b

Fingerprint Dive into the research topics of 'Unique effect of coordination of an alkene moiety in products on Ruthenium-catalyzed chemoselective C-H alkenylation'. Together they form a unique fingerprint.

Cite this

@article{d34ade71938648d0a69f5943b6b04043,

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

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",

year = "2009",

month = feb,

day = "19",

doi = "10.1021/ol802819b",

language = "English",

volume = "11",

pages = "855--858",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=64349107670&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=64349107670&partnerID=8YFLogxK

U2 - 10.1021/ol802819b

DO - 10.1021/ol802819b

M3 - Article

C2 - 19161263

AN - SCOPUS:64349107670

VL - 11

SP - 855

EP - 858

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 4

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this