Rh(II)-Catalyzed C-N Bond Formation Using Enynones and N-H Imines: An Approach to Diarylmethylamines

Ho Jun Cho; Ye Lim Kim; Ju Hyun Kim

doi:10.1021/acs.joc.2c02119

Rh(II)-Catalyzed C-N Bond Formation Using Enynones and N-H Imines: An Approach to Diarylmethylamines

Ho Jun Cho, Ye Lim Kim, Ju Hyun Kim

Department of Chemistry

Gyeongsang National University

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

5 Scopus citations

Abstract

A Rh(II)-catalyzed furyl carbene N-H insertion reaction involving an N-sp2-hybridized imine is described, which represents an atom-economical route by which to access diarylmethylamine derivatives with high efficiency and broad substrate scope. An unusual reaction mechanism is proposed, in which the rhodium catalyst plays a dual role in facilitating enynone cyclization via activation and enhancement of the nucleophilicity of the NH imine.

Original language	English
Pages (from-to)	16424-16435
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	87
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.2c02119
State	Published - 16 Dec 2022

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title = "Rh(II)-Catalyzed C-N Bond Formation Using Enynones and N-H Imines: An Approach to Diarylmethylamines",

abstract = "A Rh(II)-catalyzed furyl carbene N-H insertion reaction involving an N-sp2-hybridized imine is described, which represents an atom-economical route by which to access diarylmethylamine derivatives with high efficiency and broad substrate scope. An unusual reaction mechanism is proposed, in which the rhodium catalyst plays a dual role in facilitating enynone cyclization via activation and enhancement of the nucleophilicity of the NH imine.",

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T2 - An Approach to Diarylmethylamines

AU - Cho, Ho Jun

AU - Kim, Ye Lim

AU - Kim, Ju Hyun

PY - 2022/12/16

Y1 - 2022/12/16

N2 - A Rh(II)-catalyzed furyl carbene N-H insertion reaction involving an N-sp2-hybridized imine is described, which represents an atom-economical route by which to access diarylmethylamine derivatives with high efficiency and broad substrate scope. An unusual reaction mechanism is proposed, in which the rhodium catalyst plays a dual role in facilitating enynone cyclization via activation and enhancement of the nucleophilicity of the NH imine.

AB - A Rh(II)-catalyzed furyl carbene N-H insertion reaction involving an N-sp2-hybridized imine is described, which represents an atom-economical route by which to access diarylmethylamine derivatives with high efficiency and broad substrate scope. An unusual reaction mechanism is proposed, in which the rhodium catalyst plays a dual role in facilitating enynone cyclization via activation and enhancement of the nucleophilicity of the NH imine.

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DO - 10.1021/acs.joc.2c02119

M3 - Article

AN - SCOPUS:85143528203

SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

Rh(II)-Catalyzed C-N Bond Formation Using Enynones and N-H Imines: An Approach to Diarylmethylamines

Abstract

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