Litcius/Paper detail

Fully Automated Flow Protocol for C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Bond Formation from Tertiary Amides and Alkyl Halides

Brenda Pijper, Raúl Martín, Alberto J. Huertas-Alonso, María Lourdes Linares, Enol López, Josep Llaveria, Ángel Díaz‐Ortiz, Darren J. Dixon, António de la Hoz, Jesús Alcázar

2023Organic Letters15 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide 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.

Topics & Concepts

ChemistryAlkylHalideMedicinal chemistryStereochemistryOrganic chemistryAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and CatalysisChemical synthesis and alkaloids