Controllable, Sequential, and Stereoselective C–H Allylic Alkylation of Alkenes [post]

Ling Qin, Mohammed Sharique, Uttam Tambar
2019 unpublished
The direct conversion of C–H bonds into new C–C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from
more » ... oups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch-selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.<br>
doi:10.26434/chemrxiv.9642044 fatcat:z36pow65bzcbjb3z4yg64kxtru