TY - JOUR
T1 - Practical photocatalytic trifluoromethylation and hydrotrifluoromethylation of styrenes in batch and flow
AU - Straathof, Natan J.W.
AU - Cramer, Sten E.
AU - Hessel, Volker
AU - Noël, Timothy
PY - 2016/1/1
Y1 - 2016/1/1
N2 - Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.
AB - Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.
KW - continuous flow
KW - hydrotrifluoromethylation
KW - microreactor
KW - photoredox catalysis
KW - trifluoromethylation
UR - http://www.scopus.com/inward/record.url?scp=84997426803&partnerID=8YFLogxK
U2 - 10.1002/anie.201608297
DO - 10.1002/anie.201608297
M3 - Article
C2 - 27862770
AN - SCOPUS:84997426803
SN - 1433-7851
VL - 55
SP - 15549
EP - 15553
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 50
ER -