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Recent Advances in the Synthesis of CF 3 ‐ or HCF 2 ‐Substituted Cyclopropanes
Author(s) -
Wu WenFeng,
Lin JinHong,
Xiao JiChang,
Cao YuCai,
Ma Yanfang
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000723
Subject(s) - cyclopropanation , chemistry , reagent , cyclopropane , catalysis , transition metal , combinatorial chemistry , organic synthesis , molecule , de novo synthesis , organic chemistry , stereochemistry , enzyme , ring (chemistry)
CF 3 ‐ or HCF 2 ‐substituted cyclopropanes are of great interest in pharmaceutical chemistry and agrochemistry, and thus significant efforts have been directed towards the development of efficient methods for the installation of these motifs. This Minireview summarizes recent efforts for the construction of CF 3 ‐ or HCF 2 ‐substituted cyclopropanes. CF 3 ‐cyclopropanes are usually synthesized by a transition‐metal‐catalyzed cyclopropanation of alkenes with a trifluoromethylcarbene generated in situ from a diazocompound, CF 3 CHN 2 or CF 3 C(Ar)N 2 . The synthesis of HCF 2 ‐cyclopropanes remains largely unexplored. Some difluoromethylcarbene reagents have been developed, such as HCF 2 CHN 2 , Ph 2 S + CH 2 CF 2 H TfO − , and difluoroacetaldehyde N ‐triftosylhydrazone (DFHZ‐Tfs), and cyclopropanation of alkenes with these reagents could also occur by transition metal catalysis. These protocols may find great utility in the synthesis of biologically active molecules.