TY - JOUR
T1 - Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides
T2 - Scope, Enantioselectivity, and Mechanism
AU - Liang, Dong Dong
AU - Streefkerk, Dieuwertje E.
AU - Jordaan, Daan
AU - Wagemakers, Jorden
AU - Baggerman, Jacob
AU - Zuilhof, Han
PY - 2020/5/4
Y1 - 2020/5/4
N2 - SuFEx reactions, in which an S−F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, “Si-free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.
AB - SuFEx reactions, in which an S−F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, “Si-free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.
KW - enantioselectivity
KW - kinetics
KW - reaction mechanisms
KW - SuFEx
U2 - 10.1002/anie.201915519
DO - 10.1002/anie.201915519
M3 - Article
AN - SCOPUS:85081903029
SN - 1433-7851
VL - 59
SP - 7494
EP - 7500
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 19
ER -