Palladium-catalyzed cross-coupling of B-benzyl-9-borabicyclo[3.3.1]nonane to furnish methylene-linked biaryls.
[reaction: see text] Benzylboranes are noticeably uncommon partners within Suzuki-Miyaura coupling reactions. B-Benzyl-9-BBN was successfully coupled to a range of aryl/heteroaryl bromides, chlorides, and triflates to give pharmacologically important methylene-linked biaryl structures. Activated, deactivated, and sterically hindered substrates were successfully coupled in high yield using Pd(PPh(3))(4) or Pd(OAc)(2) with SPhos as the catalyst system.
Flaherty
Alice
A
Medicinal Chemistry, AstraZeneca R & D Charnwood, Loughborough, Leics, UK. alice.flaherty@astrazeneca.com
Trunkfield
Amy
A
Barton
William
W
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
C512810:B-benzyl-9-borabicyclo(3.3.1)nonane; D001555:Benzene Derivatives; D001880:Boranes; D001643:Bridged Bicyclo Compounds; D003432:Cross-Linking Reagents; D010165:Palladium