Intermolecular hydroamination of 1,3-dienes catalyzed by bis(phosphine)carbodicarbene-rhodium complexes

Matthew J. Goldfogel; Courtney C. Roberts; Simon J. Meek

doi:10.1021/ja502275w

Intermolecular hydroamination of 1,3-dienes catalyzed by bis(phosphine)carbodicarbene-rhodium complexes

Matthew J. Goldfogel, Courtney C. Roberts, Simon J. Meek

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

126 Scopus citations

Abstract

A carbodicarbene (CDC)-based pincer ligand scaffold is reported, along with its application to site-selective Rh(I)-catalyzed intermolecular hydroamination of 1,3-dienes with aryl and alkyl amines. To the best of our knowledge, this is the first example of the use of a well-defined CDC complex as an efficient catalyst. Transformations proceed in the presence of 1.0-5.0 mol % Rh complex at 35-120 °C; allylic amines are obtained in up to 97% yield and with >98:2 site selectivity.

Original language	English (US)
Pages (from-to)	6227-6230
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	17
DOIs	https://doi.org/10.1021/ja502275w
State	Published - Apr 30 2014
Externally published	Yes

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title = "Intermolecular hydroamination of 1,3-dienes catalyzed by bis(phosphine)carbodicarbene-rhodium complexes",

abstract = "A carbodicarbene (CDC)-based pincer ligand scaffold is reported, along with its application to site-selective Rh(I)-catalyzed intermolecular hydroamination of 1,3-dienes with aryl and alkyl amines. To the best of our knowledge, this is the first example of the use of a well-defined CDC complex as an efficient catalyst. Transformations proceed in the presence of 1.0-5.0 mol % Rh complex at 35-120 °C; allylic amines are obtained in up to 97% yield and with >98:2 site selectivity.",

author = "Goldfogel, {Matthew J.} and Roberts, {Courtney C.} and Meek, {Simon J.}",

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T1 - Intermolecular hydroamination of 1,3-dienes catalyzed by bis(phosphine)carbodicarbene-rhodium complexes

AU - Goldfogel, Matthew J.

AU - Roberts, Courtney C.

AU - Meek, Simon J.

PY - 2014/4/30

Y1 - 2014/4/30

N2 - A carbodicarbene (CDC)-based pincer ligand scaffold is reported, along with its application to site-selective Rh(I)-catalyzed intermolecular hydroamination of 1,3-dienes with aryl and alkyl amines. To the best of our knowledge, this is the first example of the use of a well-defined CDC complex as an efficient catalyst. Transformations proceed in the presence of 1.0-5.0 mol % Rh complex at 35-120 °C; allylic amines are obtained in up to 97% yield and with >98:2 site selectivity.

AB - A carbodicarbene (CDC)-based pincer ligand scaffold is reported, along with its application to site-selective Rh(I)-catalyzed intermolecular hydroamination of 1,3-dienes with aryl and alkyl amines. To the best of our knowledge, this is the first example of the use of a well-defined CDC complex as an efficient catalyst. Transformations proceed in the presence of 1.0-5.0 mol % Rh complex at 35-120 °C; allylic amines are obtained in up to 97% yield and with >98:2 site selectivity.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 17

ER -

Intermolecular hydroamination of 1,3-dienes catalyzed by bis(phosphine)carbodicarbene-rhodium complexes

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