Branched-selective intermolecular ketone α-alkylation with unactivated alkenes via an enamide directing strategy

Dong Xing; Guangbin Dong

doi:10.1021/jacs.7b08581

Branched-selective intermolecular ketone α-alkylation with unactivated alkenes via an enamide directing strategy

Dong Xing, Guangbin Dong

The University of Chicago

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

91 Scopus citations

Abstract

We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir-C migratory insertion pathway.

Original language	English
Pages (from-to)	13664-13667
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	39
DOIs	https://doi.org/10.1021/jacs.7b08581
State	Published - 4 Oct 2017
Externally published	Yes

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title = "Branched-selective intermolecular ketone α-alkylation with unactivated alkenes via an enamide directing strategy",

abstract = "We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir-C migratory insertion pathway.",

author = "Dong Xing and Guangbin Dong",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Xing, Dong

AU - Dong, Guangbin

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N2 - We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir-C migratory insertion pathway.

AB - We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir-C migratory insertion pathway.

UR - https://www.scopus.com/pages/publications/85032704757

U2 - 10.1021/jacs.7b08581

DO - 10.1021/jacs.7b08581

M3 - 文章

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AN - SCOPUS:85032704757

SN - 0002-7863

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 39

ER -

Branched-selective intermolecular ketone α-alkylation with unactivated alkenes via an enamide directing strategy

Abstract

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