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Expedient Synthesis of Functionalized Triarylmethanols through Tandem Formation of Geminal CC and CO Bonds
Author(s) -
Tian Yu,
Sui Yi,
Gu Yonghong,
Tian ShiKai
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200664
Subject(s) - chemistry , geminal , regioselectivity , trifluoroacetic acid , tandem , catalysis , palladium , combinatorial chemistry , aniline , persulfate , ammonium persulfate , intramolecular force , corrole , triple bond , manganese , medicinal chemistry , potassium persulfate , organic chemistry , double bond , materials science , polymer , composite material , polymerization
The rearrangement/oxidation of N , N ‐disubstituted anilines and the formal dehydrogenative cross‐coupling of diarylmethanols with aniline derivatives have been developed for the preparation of symmetric and unsymmetric functionalized triarylmethanols. Both reactions proceed smoothly in trifluoroacetic acid in the presence of an inexpensive oxidant (manganese dioxide or potassium persulfate) and a catalytic amount of palladium diacetate to give a range of functionalized triarylmethanols in moderate to good yields and with extremely high regioselectivity. The two unprecedented reactions involve tandem formation of geminal CC and CO bonds, and they are synthetically useful, atom‐efficient, and operationally simple.