Regioselective Copper Catalyzed Boracarboxylation Of Vinyl Arenes

Schomaker copper catalyzed recycling of halogen activating groups via 1 3 halogen migration journal of the american chemical society 10 1021 ja306446m 134 39 16131 16134 2012.

Regioselective copper catalyzed boracarboxylation of vinyl arenes. Regioselective copper catalyzed boracarboxylation of vinyl arenes article in organic letters 18 24 november 2016 with 39 reads how we measure reads. Isolated yields corrected for trace b 2 pin 2 impurity are given. This protocol is characterized by a wide scope while obviating the need for sensitive organometallic species and by an unprecedented regioselectivity pattern using simple alcohols as proton sources. An efficient copper catalyzed regioselective c h alkenylation and borylative alkylation of quinoline n oxides with vinyl arenes in the presence of pinacol diborane has been developed the reaction proceeds through the borylcupration of the vinyl arenes followed by nucleophilic attack of the resulting alkyl copper species to the quinoline n oxides.

The method has shown an extremely broad scope of substrates including difluorovinyl arenes tetrafluoroethylene tfe trifluorovinyl arenes and trifluoromethylated monofluoroalkenes. Regioselective copper catalyzed boracarboxylation of vinyl arenes trevor w. The choice of boron source was important for the efficient transformation. Scope of vinyl arene in boracarboxylation reactions astandard conditions.

A mild and user friendly ni catalyzed regioselective hydrocarboxylation of alkynes with co2 1 bar is described. A regiodivergent silacarboxylation of allenes under a co2 atmosphere with phme2si b pin as a silicon source in the presence of a copper catalyst at 70 c has been developed. Monodefluoroborylation of polyfluoroalkenes has been achieved in a regioselective manner under mild conditions via copper catalysis. Olefin borylcupration has been proposed in a variety of contexts and observed directly by sadighi and co workers for ethylene and styrene.

The regioselectivity of the reaction is successfully reversed by the proper choice of ligand. Regioselective copper catalyzed boracarboxylation of vinyl arenes with bis pinacolato diboron and carbon dioxide has been achieved. Reactions quenched with 1 m hcl aq. We envisioned that catalytic boracarboxylation of olefins could be achieved by redox neutral copper catalysis the success of the reaction would hinge upon 1 olefin borylcupration by a cu boryl species and 2 co 2 insertion into a cu alkyl species.