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Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions.

Authors :
Fan R
Liu S
Yan Q
Wei Y
Wang J
Lan Y
Tan J
Source :
Chemical science [Chem Sci] 2023 Mar 14; Vol. 14 (16), pp. 4278-4287. Date of Electronic Publication: 2023 Mar 14 (Print Publication: 2023).
Publication Year :
2023

Abstract

Boronic acids have become one of the most prevalent classes of reagents in modern organic synthesis, displaying various reactivity profiles via C-B bond cleavage. Herein, we describe the utilization of a readily available boronic acid as an efficient surrogate of hydroxide upon activation via fluoride complexation. The hitherto unknown aryne induced ring-opening reaction of cyclic sulfides and three-component coupling of fluoro-azaarenes are developed to exemplify the application value. Different from metal hydroxides or water, this novel hydroxy source displays mild activation conditions, great functionality tolerance and structural tunability, which shall engender a new synthetic paradigm and in a broad context offer new blueprints for organoboron chemistry. Detailed computational studies also recognize the fluoride activation mode, provide in-depth insights into the unprecedented mechanistic pathway and elucidate the reactivity difference of ArB(OH) <subscript> x </subscript> F <subscript> y </subscript> complexes, which fully support the experimental data.<br />Competing Interests: There are no conflicts to declare.<br /> (This journal is © The Royal Society of Chemistry.)

Details

Language :
English
ISSN :
2041-6520
Volume :
14
Issue :
16
Database :
MEDLINE
Journal :
Chemical science
Publication Type :
Academic Journal
Accession number :
37123174
Full Text :
https://doi.org/10.1039/d3sc00072a