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Copper‐Catalyzed Highly Selective Protoboration of CF 3 ‐Containing 1,3‐Dienes
Author(s) -
Wu Juanjuan,
Wu Hongli,
Li Xinzhi,
Liu Xinyu,
Zhao Qian,
Huang Genping,
Zhang Chun
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105896
Subject(s) - reagent , catalysis , chemistry , allylic rearrangement , diene , functional group , ligand (biochemistry) , boron , conjugated system , copper , combinatorial chemistry , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry , receptor , biochemistry , natural rubber , polymer
The copper‐catalyzed highly selective protoboration of CF 3 ‐containing conjugated diene with proton source and B 2 Pin 2 has been developed. This chemistry could suppress the well‐known defluorination and provide borated reagents with an intact CF 3 ‐group. Further studies indicated that the functional group tolerance of this chemistry is very well, and the products could be used as versatile precursors for different types of transformations. Importantly, using chiral diphosphine ligand, we have developed the first example for using such starting material to synthesis allylic boron‐reagents which bearing a CF 3 ‐containing chiral center. Notably, the reaction mechanism was intensively studied by DFT calculations, which could reveal the reason that defluorination was inhibited.