Premium
Iridium‐Catalyzed Synthesis of Diaryl Ethers by Means of Chemoselective CF Bond Activation and the Formation of BF Bonds
Author(s) -
Chen Jianping,
Zhao Keyan,
Ge Bingyang,
Xu Chongying,
Wang Dawei,
Ding Yuqiang
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403130
Subject(s) - iridium , catalysis , chemistry , cleave , bond cleavage , transition metal , ether , fluoride , polymer chemistry , fluorine , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , inorganic chemistry , enzyme
Transition‐metal‐catalyzed CF activation, in comparison with CH activation, is more difficult to achieve and therefore less fully understood, mainly because carbon–fluorine bonds are the strongest known single bonds to carbon and have been very difficult to cleave. Transition‐metal complexes are often more effective at cleaving stronger bonds, such as C(sp 2 )X versus C(sp 3 )X. Here, the iridium‐catalyzed CF activation of fluorarenes was achieved through the use of bis(pinacolato)diboron with the formation of the BF bond and self‐coupling. This strategy provides a convenient method with which to convert fluoride aromatic compounds into symmetrical diaryl ether compounds. Moreover, the chemoselective products of the CF bond cleavage were obtained at high yields with the CBr and CCl bonds remaining.