- A tuned bicyclic proazaphosphatrane for catalytically enhanced n-arylation reactions with aryl chlorides
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The N-arylation of various amines with aryl chlorides proceeded in good-to-excellent yields in the presence of P[N{(p-NMe2)C6H4CH2}CH2CH2]3N (1e, a new electron-rich proazaphosphatrane ligand) and small amounts of Pd2(dba)3 (dba = dibenzylideneacetone). This catalytic system was also very effective for the synthesis of carbazoles. An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.
- Kim, So Han,Kim, Min,Verkade, John G.,Kim, Youngjo
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- Highly efficient ligands for the palladium-assisted double N-arylation of primary amines for one-sep construction of carbazoles
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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(O) (Pd2dba3) and the proazaphosphatrane P(i-BuNCH 2CH2)3N (8) or its derivative (t-Bu) 2P=N-P(iBuNCH2CH2)3N (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, electronrich, electron-deficient, and sterically hindered anilines as well as aliphatic amines.
- Zhou, Yibo,Verkade, John G.
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supporting information; experimental part
p. 616 - 620
(2010/07/03)
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