One-pot synthesis of trisubstituted conjugated dienes via sequential Suzuki-Miyaura cross-coupling with alkenyl- and alkyltrifluoroborates.
The sequential, stereoselective disubstitution of 1,1-dibromoalkenes using a variety of alkenyltrifluoroborates followed by alkyltrifluoroborates in the presence of Pd(PPh3)4 is described. This synthetic method proceeds smoothly in one pot under mild reaction conditions to provide the corresponding trisubstituted, conjugated dienes in excellent yield. Moreover, the method is operationally very simple because the organotrifluoroborates are stable in air, and the byproducts are innocuous inorganic salts.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Yokoyama
Yasuo
Y
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000466:Alkadienes; D000475:Alkenes; D001881:Borates