Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 4, Pages 616-620Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900846
Keywords
biaryls; carbazoles; C-N coupling; heterocycles; palladium
Categories
Funding
- National Science Foundation [0750463]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0750463] Funding Source: National Science Foundation
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A highly efficient one-pot synthesis of carbazoles via palladium-catalyzed double N-arylation of primary amines with 2,2'-dihalobiphenyls is described using a catalyst system comprised of tris(dibenzylideneacetone)dipalladium(0) (Pd(2)dba(3)) and the proazaphosphatrane P(i-BuNCH2CH2)(3)N (8) or its derivative (t-Bu)(2)P=N-P(i-BuNCH2CH2)(3)N (9a) as the ligand. The process is effective for double N-arylation of 2,2'-biphenyl dibromide, diiodide, and even dichloride with a variety of primary amines including neutral, electron-rich, electron-deficient, and sterically hindered anilines as well as aliphatic amines.
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