Synthesis of Hindered Anilines: Three-Component Coupling of Arylboronic Acids, tert-Butyl Nitrite, and Alkyl Bromides.
The synthesis of sterically hindered amines has been a significant challenge in organic chemistry. Herein, we report a modular, three-component coupling that constructs two carbon-nitrogen bonds including a sterically hindered Csp3-N bond using commercially available materials. This process uses an earth-abundant copper catalyst and mild reaction conditions, allowing access to a variety of complex aromatic amines.
Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
David J
DJ
Fisher
Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
James B
JB
Shaum
Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
C Landon
CL
Mills
Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
Javier
J
Read de Alaniz
D000473:Alkanes / Q000737:chemistry; D000478:Alkylation; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009573:Nitrites / Q000737:chemistry*; D013867:Thiohydantoins / Q000138:chemical synthesis / Q000737:chemistry
C583810:4-methoxyphenylboronic acid; D000473:Alkanes; D000814:Aniline Compounds; D001897:Boronic Acids; D006842:Hydrocarbons, Brominated; D009573:Nitrites; D013867:Thiohydantoins; C024225:n-butyl nitrite; D003300:Copper