5080-10-4Relevant articles and documents
Simple and efficient metal-free hydroarylation and hydroalkylation using strongly acidic ion-exchange resin
Das, Biswanath,Krishnaiah, Martha,Laxminarayana, Keetha,Damodar, Kongara,Kumar, D. Nandan
experimental part, p. 42 - 43 (2009/12/02)
Higly efficient hydroarylation and hydroalkylation of styrenes with various arenes and 1,3-dicarbonyl compounds respectively have been developed using Amberlyst-15 as a heterogeneous catalyst. The excellent yields, short reaction times, and high selectivity are the advantages of this method. The C-H functionalization has been achieved here under metal-free conditions. Copyright
A new approach to carbon-carbon bond formation: development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes
Gligorich, Keith M.,Iwai, Yasumasa,Cummings, Sarah A.,Sigman, Matthew S.
experimental part, p. 5074 - 5083 (2009/12/01)
Alkenes are attractive starting materials for organic synthesis and the development of new selective functionalization reactions is desired. Previously, our laboratory discovered a unique Pd-catalyzed hydroalkoxylation reaction of styrenes containing a phenol. Based upon deuterium labeling experiments, a mechanism involving an aerobic alcohol oxidation coupled to alkene functionalization was proposed. These results inspired the development of a new Pd-catalyzed reductive coupling reaction of alkenes and organometallic reagents that generates a new carbon-carbon bond. Optimization of the conditions for the coupling of both organostannanes and organoboronic esters is described and the initial scope of the transformation is presented. Additionally, several mechanistic experiments are outlined and support the rationale for the development of the reaction based upon coupling alcohol oxidation to alkene functionalization.
Palladium-catalyzed reductive coupling of styrenes and organostannanes under aerobic conditions
Gligorich, Keith M.,Cummings, Sarah A.,Sigman, Matthew S.
, p. 14193 - 14195 (2008/09/18)
We report a highly regioselective PdII-catalyzed reductive coupling of an alkene with an organostannane using a tandem alcohol oxidation under aerobic conditions. Both aryl- and vinylstannanes are competent coupling partners with a variety of s