KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N -Sulfinylimines Using HFC-125 - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2022

KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N -Sulfinylimines Using HFC-125

Résumé

A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4-tBu.

Domaines

Chimie organique
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Dates et versions

hal-04234835 , version 1 (10-10-2023)

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Citer

Yuji Sumii, Hiroto Iwasaki, Yamato Fujihira, Elsayed Mahmoud, Hiroaki Adachi, et al.. KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N -Sulfinylimines Using HFC-125. Journal of Organic Chemistry, 2022, 87 (23), pp.15806-15819. ⟨10.1021/acs.joc.2c01821⟩. ⟨hal-04234835⟩
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