Journal
ACS CATALYSIS
Volume 12, Issue 14, Pages 8331-8340Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c01835
Keywords
hydroamination; iridium catalysis; rhodium catalysis; diamine; regiodivergent
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Funding
- NIH [R35 GM125029]
- Sloan Foundation [FG-2016-6568]
- Welch Foundation [F-199420190330]
- Novartis
- Eli Lilly
- University of Texas at Austin
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The Ir-catalyzed regioselective hydroamination of allyl amines and the catalyst-controlled regiodivergent hydroamination of homoallylic amines with aniline nucleophiles have been reported. These reactions can selectively synthesize diamines at different positions, and exhibit good reaction yields.
The Ir-catalyzed regioselective hydroamination of allyl amines as well as the catalyst-controlled regiodivergent hydroamination of homoallylic amines with aniline nucleophiles is reported. These directed hydroamination reactions afford a variety of 1,2-, 1,3-, and 1,4-diamines in good to excellent yields and high regio- and chemoselectivities. Mechanistic investigations suggest that the reactions are proceeding through an oxidative addition into the ArHN-H bond and that the observed regioselectivity is due to the selective formation of a five- or six-membered metallacyclic intermediate depending on the catalyst employed.
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