Journal
ACS CATALYSIS
Volume 11, Issue 20, Pages 12417-12422Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c03113
Keywords
nitroarene; nitrosoarene; aryl boronic acid; cross-coupling; copper
Categories
Funding
- National Institutes of Health, NIGMS [R01GM138388]
- National Science Foundation [CHE-1564959]
Ask authors/readers for more resources
A simple copper-catalyzed reaction involving nitroarenes and aryl boronic acids to form diarylamines has been described, with phenyl silane as the stoichiometric terminal reductant. The cross-coupling reaction requires low concentrations of CuX and diphosphine, tolerates a wide range of functional groups, and proceeds via a nitrosoarene intermediate catalyzed by copper.
The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C-NAr bond formation of the nitrosoarene with the aryl boronic acid.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available