Synthesis of highly substituted 1,3-dienes, 1,3,5-trienes, and 3,6-disubstituted cyclohexenes by the palladium-catalyzed coupling of organic halides, internal alkynes or 1,3-cyclohexadienes, and organoboranes
作者:Xiaoxia Zhang、Richard C. Larock
DOI:10.1016/j.tet.2010.03.119
日期:2010.6
A number of highly substituted 1,3-dienes and 1,3,5-trienes have been stereoselectively prepared in moderate to good yields by the coupling of vinylic iodides, internal alkynes, and organoboranes in the presence of a palladium catalyst. Optimal reaction conditions for different organoboron substrates have been developed. The analogous three-component coupling of aryl halides, 1,3-cyclohexadiene, and
Regioselective Synthesis of β-Aryl- and β-Amino-Substituted Aliphatic Esters by Rhodium-Catalyzed Tandem Double-Bond Migration/Conjugate Addition
作者:Dominik M. Ohlmann、Lukas J. Gooßen、Markus Dierker
DOI:10.1002/chem.201100654
日期:2011.8.16
unsaturated esters. Once the double‐bond is in conjugation with the carboxylate group, they also catalyze the Michael addition of carbon and nitrogen nucleophiles. In the presence of these catalysts, unsaturated carboxylates enter a dynamic equilibrium of positional and geometrical double‐bond isomers. The conjugated species are continuously removed through 1,4‐additions with formation of β‐amino esters or
Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents
作者:Marie S. T. Morin、Yingdong Lu、Daniel A. Black、Bruce A. Arndtsen
DOI:10.1021/jo202339v
日期:2012.2.17
A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes to form α-substituted amides is described. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and represent a useful generalization of the Petasis reaction.