syn-selective 1,2-carboboration and -silylation pre-print online

Our latest work on directed alkene functionalization appears online today as a preprint in ChemRxiv. Specifically we describe a method for Pd(0)-catalyzed alkene syn-1,2-carboboration and -silylation, allowing streightforward access to structural complex alkylboronates and -silanes. Notable aspects of the method include its tolerance for all different alkene substitution patterns (mono-, di-, tri-, and tetrasubstituted alkenes), with the regioselectivity completely dictated by the directing group. Additionally, electron-rich heterocycles, such as indole, can also participate in this reaction; undergoing dearomative 1,2-difunctionalization. We further show that a chiral bidentate directing group can be used in place of the standard 8-aminoquinoline auxiliary to allow for control of absolute and relative stereochemistry in the reactions. Congrats to all of the coauthors from the Engle lab: Zhen, Jiahao, Xiaohan, and Yang (particularly undergrad co-authors Jiahao and Xiaohan). Thanks too to our BMS collaborators and organoboron grand masters, Ryan and Matt. Well done, team! (For a link to the article, click here.)