TY - JOUR
T1 - 1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds
T2 - N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources
AU - Xiao, Qing
AU - He, Qijie
AU - Li, Juncheng
AU - Wang, Jun
N1 - Funding information:
We gratefully thank the startup fund and faculty research grant (FRG-SUSTC1501A-58) from South University of Science and Technology of China for financial support.
Publisher copyright:
© 2015 American Chemical Society
PY - 2015/12/10
Y1 - 2015/12/10
N2 - A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves as both the nitrogen and SCF3 sources. In the presence of DABCO (1,4-diazabicyclo[2.2.2]octane), the nitrogen and SCF3 groups can be incorporated into α,β-unsaturated carbonyl compounds easily and give versatile β-amino ketones and esters in good yields. This difunctionalization reaction features mild reaction conditions, high atom-economy, and efficient access to α-SCF3 amino acids.
AB - A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves as both the nitrogen and SCF3 sources. In the presence of DABCO (1,4-diazabicyclo[2.2.2]octane), the nitrogen and SCF3 groups can be incorporated into α,β-unsaturated carbonyl compounds easily and give versatile β-amino ketones and esters in good yields. This difunctionalization reaction features mild reaction conditions, high atom-economy, and efficient access to α-SCF3 amino acids.
UR - https://www.scopus.com/inward/record.uri?eid=2-s2.0-84952685494&doi=10.1021%2facs.orglett.5b03116&partnerID=40&md5=1e7de4e27867252b90f41adbd734cd32
U2 - 10.1021/acs.orglett.5b03116
DO - 10.1021/acs.orglett.5b03116
M3 - Journal article
SN - 1523-7060
VL - 17
SP - 6090
EP - 6093
JO - Organic Letters
JF - Organic Letters
IS - 24
ER -