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

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 r...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-10, Vol.139 (40), p.14049-14052
Main Authors: Yang, Xiao-Hui, Lu, Alexander, Dong, Vy M
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Amination
Amines - chemical synthesis
Amines - chemistry
Catalysis
Ligands
Mandelic Acids - chemical synthesis
Mandelic Acids - chemistry
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Rhodium - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.7b09188