Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis

Yoshiaki Nakao; Hiroaki Idei; Kyalo Stephen Kanyiva; Tamejiro Hiyama

doi:10.1021/ja901153s

Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis

Yoshiaki Nakao^*, Hiroaki Idei, Kyalo Stephen Kanyiva, Tamejiro Hiyama

^*Corresponding author for this work

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

125 Citations (Scopus)

Abstract

Formamides are found to undergo addition reactions across alkynes and 1,3-dienes by nickel/Lewis acid catalysis to give a variety of α, β- and β,γ-unsaturated amides with stereo- and regioselectivity. Intramolecular insertion reactions of olefins into the C-H bonds of formamides also proceed under similar conditions. The presence of Lewis acid cocatalysts is crucial, and formamide coordination to the Lewis acid is considered to be responsible for the activation of their formyl C-H bonds probably through oxidative addition to nickel(0).

Original language	English
Pages (from-to)	5070-5071
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	14
DOIs	https://doi.org/10.1021/ja901153s
Publication status	Published - 2009 Apr 15
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja901153s

Cite this

@article{3b94d4896e9a40948d24436ce5278fac,

title = "Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis",

abstract = "Formamides are found to undergo addition reactions across alkynes and 1,3-dienes by nickel/Lewis acid catalysis to give a variety of α, β- and β,γ-unsaturated amides with stereo- and regioselectivity. Intramolecular insertion reactions of olefins into the C-H bonds of formamides also proceed under similar conditions. The presence of Lewis acid cocatalysts is crucial, and formamide coordination to the Lewis acid is considered to be responsible for the activation of their formyl C-H bonds probably through oxidative addition to nickel(0).",

author = "Yoshiaki Nakao and Hiroaki Idei and Kanyiva, {Kyalo Stephen} and Tamejiro Hiyama",

year = "2009",

month = apr,

day = "15",

doi = "10.1021/ja901153s",

language = "English",

volume = "131",

pages = "5070--5071",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis

AU - Nakao, Yoshiaki

AU - Idei, Hiroaki

AU - Kanyiva, Kyalo Stephen

AU - Hiyama, Tamejiro

PY - 2009/4/15

Y1 - 2009/4/15

N2 - Formamides are found to undergo addition reactions across alkynes and 1,3-dienes by nickel/Lewis acid catalysis to give a variety of α, β- and β,γ-unsaturated amides with stereo- and regioselectivity. Intramolecular insertion reactions of olefins into the C-H bonds of formamides also proceed under similar conditions. The presence of Lewis acid cocatalysts is crucial, and formamide coordination to the Lewis acid is considered to be responsible for the activation of their formyl C-H bonds probably through oxidative addition to nickel(0).

AB - Formamides are found to undergo addition reactions across alkynes and 1,3-dienes by nickel/Lewis acid catalysis to give a variety of α, β- and β,γ-unsaturated amides with stereo- and regioselectivity. Intramolecular insertion reactions of olefins into the C-H bonds of formamides also proceed under similar conditions. The presence of Lewis acid cocatalysts is crucial, and formamide coordination to the Lewis acid is considered to be responsible for the activation of their formyl C-H bonds probably through oxidative addition to nickel(0).

UR - http://www.scopus.com/inward/record.url?scp=67849087115&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67849087115&partnerID=8YFLogxK

U2 - 10.1021/ja901153s

DO - 10.1021/ja901153s

M3 - Article

C2 - 19351203

AN - SCOPUS:67849087115

SN - 0002-7863

VL - 131

SP - 5070

EP - 5071

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 14

ER -

Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this