Continuous‐Flow Synthesis of Biaryls by Negishi Cross‐Coupling of Fluoro‐ and Trifluoromethyl‐Substituted (Hetero)arenes. (26th July 2016)

• Record Type: Journal Article
• Authors: Roesner, Stefan; Buchwald, Stephen L.
• Is Part Of: Angewandte Chemie. Volume 128:Number 35(2016)
• Page Start: 10619
• Page End: 10623
• Publication Date: 2016-07-26
• Subjects: Biaryle -- Durchflusschemie -- Kreuzkupplungen -- Palladium -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201605584
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A continuous‐flow method for the regioselective arylation of fluoroarenes and fluoropyridines has been developed. The telescoped procedure reported here consists of a three‐step metalation, zincation, and Negishi cross‐coupling sequence, providing efficient access to a variety of functionalized 2‐fluorobiaryl products. Precise temperature control of the metalation step, made possible by continuous‐flow technology, allowed for the efficient preparation of the arylated products in high yields and short residence times. Additionally, several examples of the regioselective arylation of benzotrifluoride derivatives are also provided.