Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents

Shingo Ito; Yu Ichi Fujiwara; Eiichi Nakamura; Masaharu Nakamura

doi:10.1021/ol901610a

Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents

Shingo Ito, Yu Ichi Fujiwara, Eiichi Nakamura, Masaharu Nakamura^*

^*Corresponding author for this work

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

84 Citations (Scopus)

Abstract

Iron-catalyzed cross-coupling reactions of primary and secondary alkyl sulfonates with arylzinc reagents proceed smoothly In the presence of excess TMEDA and a concomitant magnesium salt. The arylzinc reagents are prepared from the corresponding aryllithium or magnesium reagents with ZnI₂. The In situ formation of alkyl Iodides and consecutive rapid cross-coupling avoids discrete preparation of the unstable secondary alkyl halides and also achieves high product selectivity.

Original language	English
Pages (from-to)	4306-4309
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	19
DOIs	https://doi.org/10.1021/ol901610a
Publication status	Published - Oct 1 2009
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol901610a

Cite this

@article{b58b368253d449b5990a4e1da31f36f3,

title = "Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents",

abstract = "Iron-catalyzed cross-coupling reactions of primary and secondary alkyl sulfonates with arylzinc reagents proceed smoothly In the presence of excess TMEDA and a concomitant magnesium salt. The arylzinc reagents are prepared from the corresponding aryllithium or magnesium reagents with ZnI2. The In situ formation of alkyl Iodides and consecutive rapid cross-coupling avoids discrete preparation of the unstable secondary alkyl halides and also achieves high product selectivity.",

author = "Shingo Ito and Fujiwara, {Yu Ichi} and Eiichi Nakamura and Masaharu Nakamura",

year = "2009",

month = oct,

day = "1",

doi = "10.1021/ol901610a",

language = "English",

volume = "11",

pages = "4306--4309",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents

AU - Ito, Shingo

AU - Fujiwara, Yu Ichi

AU - Nakamura, Eiichi

AU - Nakamura, Masaharu

PY - 2009/10/1

Y1 - 2009/10/1

N2 - Iron-catalyzed cross-coupling reactions of primary and secondary alkyl sulfonates with arylzinc reagents proceed smoothly In the presence of excess TMEDA and a concomitant magnesium salt. The arylzinc reagents are prepared from the corresponding aryllithium or magnesium reagents with ZnI2. The In situ formation of alkyl Iodides and consecutive rapid cross-coupling avoids discrete preparation of the unstable secondary alkyl halides and also achieves high product selectivity.

AB - Iron-catalyzed cross-coupling reactions of primary and secondary alkyl sulfonates with arylzinc reagents proceed smoothly In the presence of excess TMEDA and a concomitant magnesium salt. The arylzinc reagents are prepared from the corresponding aryllithium or magnesium reagents with ZnI2. The In situ formation of alkyl Iodides and consecutive rapid cross-coupling avoids discrete preparation of the unstable secondary alkyl halides and also achieves high product selectivity.

UR - http://www.scopus.com/inward/record.url?scp=70349902849&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70349902849&partnerID=8YFLogxK

U2 - 10.1021/ol901610a

DO - 10.1021/ol901610a

M3 - Article

C2 - 19731937

AN - SCOPUS:70349902849

SN - 1523-7060

VL - 11

SP - 4306

EP - 4309

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this