Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent.
[reaction: see text]. A simple, palladium-catalyzed method to convert aryl halides to the parent anilines using lithium bis(trimethylsilyl)amide (LiN(SiMe3)2) is reported. The reaction is catalyzed by Pd(dba)2 and P(t-Bu)3 and can be run with as little as 0.2 mol % of catalyst. The reaction is faster than competing generation of benzyne intermediates and, therefore, provides the aniline products regiospecifically.
Lee
S
S
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
Jørgensen
M
M
Hartwig
J F
JF
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D014297:Trimethylsilyl Compounds
D000588:Amines; D006219:Halogens; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C437125:lithium bis(trimethylsilyl)amide; D010165:Palladium; D000641:Ammonia