Intermolecular Hydroamination of 1,3-Dienes to Generate Homoallylic Amines

Xiao Hui Yang; Alexander Lu; Vy M. Dong

doi:10.1021/jacs.7b09188

Intermolecular Hydroamination of 1,3-Dienes to Generate Homoallylic Amines

Xiao Hui Yang, Alexander Lu, Vy M. Dong^*

^*Corresponding author for this work

University of California at Irvine

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

89 Citations (Scopus)

Abstract

We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Brønsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.

Original language	English
Pages (from-to)	14049-14052
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	40
DOIs	https://doi.org/10.1021/jacs.7b09188
Publication status	Published - 11 Oct 2017
Externally published	Yes

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10.1021/jacs.7b09188

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abstract = "We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Br{\o}nsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.",

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AB - We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Brønsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.

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Intermolecular Hydroamination of 1,3-Dienes to Generate Homoallylic Amines

Abstract

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