Modular synthesis of α-Arylated carboxylic acids, esters and amides via photocatalyzed triple C−F bond cleavage of methyltrifluorides

Sifan Li, Paul Davies, Wei Shu

Research output: Contribution to journalArticlepeer-review

Abstract

α-Arylated carboxylic acids and amides are widespread motifs in bioactive molecules and important building blocks in chemical synthesis. Thus, straightforward and rapid access to such structures is highly desirable. Here we report an organophotocatalytic multicomponent synthesis of α-arylated carboxylic acids, esters and amides from exhaustive defluorination of α-trifluoromethyl alkenes in the presence of alkyltrifluoroborates, water and nitrogen/oxygen nucleophiles. This operationally simple strategy features a unified access to functionally diverse α-arylated carboxylic acids, esters, primary, secondary, and tertiary amides through backbone assembly from simple starting materials enabled by consecutive C-F bond functionalization at room temperature. Preliminary mechanistic investigations reveal the reaction operates through a radical-triggered three-step cascade process, which involves distinct mechanisms for each defluorinative functionalization of C−F bond.
Original languageEnglish
JournalChemical Science
DOIs
Publication statusAccepted/In press - 12 May 2022

Bibliographical note

Accepted Manuscript available online 12/05/2022.

Fingerprint

Dive into the research topics of 'Modular synthesis of α-Arylated carboxylic acids, esters and amides via photocatalyzed triple C−F bond cleavage of methyltrifluorides'. Together they form a unique fingerprint.

Cite this