Rhenium-catalyzed insertion of terminal alkenes into a C(sp2)-H bond and successive transfer hydrogenation

Yoichiro Kuninobu; Takahiro Nakahara; Peng Yu; Kazuhiko Takai

doi:10.1016/j.jorganchem.2010.09.064

Rhenium-catalyzed insertion of terminal alkenes into a C(sp²)-H bond and successive transfer hydrogenation

Yoichiro Kuninobu, Takahiro Nakahara, Peng Yu, Kazuhiko Takai

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

8 Citations (Scopus)

Abstract

Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)₄]_n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C-H bond at the ortho-position of the imino group of the aromatic aldimine followed by sequential β-hydride elimination from the formed alkyl rhenium intermediate and then by hydrogenation of the imino group of the aldimine.

Original language	English
Pages (from-to)	348-351
Number of pages	4
Journal	Journal of Organometallic Chemistry
Volume	696
Issue number	1
DOIs	https://doi.org/10.1016/j.jorganchem.2010.09.064
Publication status	Published - Jan 1 2011
Externally published	Yes

Keywords

Aldimine
Alkene
Hydrogen transfer
Insertion
Rhenium

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2010.09.064

Cite this

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title = "Rhenium-catalyzed insertion of terminal alkenes into a C(sp2)-H bond and successive transfer hydrogenation",

abstract = "Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)4]n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C-H bond at the ortho-position of the imino group of the aromatic aldimine followed by sequential β-hydride elimination from the formed alkyl rhenium intermediate and then by hydrogenation of the imino group of the aldimine.",

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T1 - Rhenium-catalyzed insertion of terminal alkenes into a C(sp2)-H bond and successive transfer hydrogenation

AU - Kuninobu, Yoichiro

AU - Nakahara, Takahiro

AU - Yu, Peng

AU - Takai, Kazuhiko

PY - 2011/1/1

Y1 - 2011/1/1

N2 - Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)4]n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C-H bond at the ortho-position of the imino group of the aromatic aldimine followed by sequential β-hydride elimination from the formed alkyl rhenium intermediate and then by hydrogenation of the imino group of the aldimine.

AB - Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)4]n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C-H bond at the ortho-position of the imino group of the aromatic aldimine followed by sequential β-hydride elimination from the formed alkyl rhenium intermediate and then by hydrogenation of the imino group of the aldimine.

KW - Aldimine

KW - Alkene

KW - Hydrogen transfer

KW - Insertion

KW - Rhenium

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