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Cross‐Coupling of Alkyl Redox‐Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis
Author(s) -
Mao Runze,
Balon Jonathan,
Hu Xile
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804873
Subject(s) - alkyl , chemistry , photoredox catalysis , electrophile , nucleophile , benzophenone , alkylation , organic chemistry , combinatorial chemistry , catalysis , primary (astronomy) , amination , coupling reaction , photocatalysis , physics , astronomy
Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal‐catalyzed cross‐coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross‐coupling of alkyl N ‐hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone‐derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.