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Facile Synthesis of 2‐Fluorobenzofurans: 5‐ endo ‐ trig Cyclization of β,β‐Difluoro‐ o‐ hydroxystyrenes
Author(s) -
Morioka Ryutaro,
Fujita Takeshi,
Ichikawa Junji
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000159
Subject(s) - chemistry , microwave irradiation , nucleophile , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
Efficient synthetic methods were established for obtaining 2‐fluorobenzofurans involving various substituents. Upon being treated with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene under microwave irradiation, the α‐unsubstituted β,β‐difluoro‐ o ‐hydroxystyrenes underwent nucleophilic 5‐ endo ‐ trig cyclization to afford the corresponding 2‐fluorobenzofurans in high yields. Furthermore, 2‐fluoro‐3‐iodobenzofuran was successfully synthesized, and its transformation to various 3‐substituted 2‐fluorobenzofurans was demonstrated.