Ligand‐Controlled, Tunable Copper‐Catalyzed Radical Divergent Trifluoromethylation of Unactivated Cycloalkenes

The Cu‐catalyzed high‐chemoselective trifluoromethylation reactions of unactivated cycloalkenes via the modulation of appropriate ligands have been explored. The Cu(I)/appropriate ligands‐catalytic systems overcome the key challenge in differentiating two pathways involving radical intermediates and...

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Published inAdvanced synthesis & catalysis Vol. 363; no. 23; pp. 5284 - 5291
Main Authors Wang, Qi, Zang, Zhong‐Lin, Jie, Mi, Luo, Li‐Hua, Yang, Dan, Zhou, Cheng‐He, Cai, Gui‐Xin
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.12.2021
Wiley Subscription Services, Inc
Subjects
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Chlorine
Copper
cyclization
Dichloroethane
fluorine
ligand effects
Ligands
Organic chemistry
Organic compounds
Physical Sciences
Science & Technology
synthetic methods
SODIUM TRIFLUOROMETHANESULFINATE
ONE-POT
BOND FORMATION
C-H FUNCTIONALIZATION
OXIDATIVE TRIFLUOROMETHYLATION
cyclization
chlorine
OLEFINS
ARYL
EFFICIENT
synthetic methods
TERMINAL ALKENES
ligand effects
fluorine
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Summary:The Cu‐catalyzed high‐chemoselective trifluoromethylation reactions of unactivated cycloalkenes via the modulation of appropriate ligands have been explored. The Cu(I)/appropriate ligands‐catalytic systems overcome the key challenge in differentiating two pathways involving radical intermediates and provide a ligand‐controlled approach for site‐specific spiro‐aryltrifluoromethylation and chlorotrifluoromethylation to afford trifluoromethylated spiro‐tetrahydroquinoline compounds and vicinal Cl‐containing trifluoromethyl cycloalkanes. Moreover, compared with reported chlorine sources, 1,2‐dichloroethane is used as more green and economical feedstock for chlorotrifluoromethylation.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101016