Construction of congested Csp3-Csp3 bonds by a formal Ni-catalyzed alkylboration

Through the combination of a Ni-catalyzed alkene alkenylboration followed by hydrogenation, the synthesis of congested Csp(3)-Csp(3)-bonds can be achieved. Conditions have been identified that allow for the use of both alkenyl-bromides and -triflates. In addition, the hydrogenation creates another opportunity for stereocontrol, thus allowing access to multiple stereoisomers of the product. Finally, the method is demonstrated in the streamlined synthesis of a biologically relevant molecule.

Automated summary

By combining a Ni-catalyzed alkene alkenylboration with hydrogenation, congested Csp(3)-Csp(3) bonds can be synthesized, allowing for the use of both alkenyl-bromides and -triflates. The hydrogenation also provides an opportunity for stereocontrol, leading to multiple stereoisomers of the product. This method has been demonstrated in the streamlined synthesis of a biologically relevant molecule.