Room-temperature Pd-catalyzed amidation of aryl bromides using tert-butyl carbamate.
The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tert-butyl carbamate is described. For the first time, this process can be conducted at room temperature (17-22 degrees C) using a combination of Pd(2)dba(3).CHCl(3) and a monodentate ligand, tert-butyl X-Phos. Use of sodium tert-butoxide is crucial to the success of the reaction, which proceeds in 43-83% yield.
Bhagwanth
Swapna
S
Department of Medicinal Chemistry, Cancer Research, Oncology R&D, GlaxoSmithKline, Research Triangle Park, North Carolina 27709, USA.
Waterson
Alex G
AG
Adjabeng
George M
GM
Hornberger
Keith R
KR
D000814:Aniline Compounds / Q000138:chemical synthesis*; D001969:Bromobenzenes / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013696:Temperature
D000814:Aniline Compounds; D001969:Bromobenzenes; D002219:Carbamates; D009942:Organometallic Compounds; D010165:Palladium