Fully Automated Flow Protocol for C(sp 3 )-C(sp 3 ) Bond Formation from Tertiary Amides and Alkyl Halides.

Herein, we present a novel C(sp 3 )-C(sp 3 ) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule synthesis on the gram-scale starting from bench-stable reagents. Additionally, excellent chemoselectivity and functional group tolerance make it ideal for late-stage diversification of druglike molecules.