1,2-Carbofluorination of unactivated alkenes enabled by a sterically tuned auxiliary design – Pre-print now online

In the latest story arising from our lab’s Bristol Myers Squibb collaboration, we report the design of a sterically tuned directing auxiliary, picolinyl-α,α-gem-diethyl amine (PDE), which promotes C(sp3)–F reductive elimination from a Pd(IV) intermediate and enables efficient syn-1,2-carbofluorination of unactivated alkenes under Pd(II)/Pd(IV) catalysis. The improved yield of PDE versus classical directing auxiliaries, such as 8-aminoquinoline (AQ) and 2-(pyridin-2-yl)isopropyl (PIP) is rationalized by comparison of % buried volume (%VBur) across the three pre-reductive-elimination intermediates. Great work by Zhonglin, Luke, Zi-Qi, and Nana on the Scripps side and Geraint from BMS Discovery Chemistry.

For a link to the pre-print in ChemRxiv, click here: https://chemrxiv.org/engage/chemrxiv/article-details/62608592d048ed03304b657d