Open AccessBismuth(iii ) triflate as a novel and efficient activator for glycosyl halides
Author(s) -
Hayley B. Steber,
Yashapal Singh,
Alexei V. Demchenko
Publication year - 2021
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/d1ob00093d
Subject(s) - glycosyl , trifluoromethanesulfonate , bismuth , halide , chemistry , catalysis , activator (genetics) , combinatorial chemistry , organic chemistry , biochemistry , gene
Presented herein is the discovery that bismuth(iii) trifluoromethanesulfonate (Bi(OTf) 3 ) is an effective catalyst for the activation of glycosyl bromides and glycosyl chlorides. The key objective for the development of this methodology is to employ only one promoter in the lowest possible amount and to avoid using any additive/co-catalyst/acid scavenger except molecular sieves. Bi(OTf) 3 works well in promoting the glycosidation of differentially protected glucosyl, galactosyl, and mannosyl halides with many classes of glycosyl acceptors. Most reactions complete within 1 h in the presence of only 35% of green and light-stable Bi(OTf) 3 catalyst.