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Combination of Tetrabutylammonium Iodide (TBAI) with tert ‐Butyl Hydroperoxide (TBHP): An Efficient Transition‐Metal‐Free System to Construct Various Chemical Bonds
Author(s) -
Chen Rongxiang,
Chen Jijun,
Zhang Jie,
Wan Xiaobing
Publication year - 2018
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201700069
Subject(s) - chemistry , chemoselectivity , catalysis , allylic rearrangement , iodide , iodine , organic chemistry , transition metal , medicinal chemistry
In this account, we describe our recent progress on transition‐metal‐free‐catalyzed cross‐coupling reactions using tetrabutylammonium iodide (TBAI) as the catalyst and tert ‐butyl hydroperoxide (TBHP) as the oxidant. A rich variety of important organic compounds including α‐acyloxy ethers, tert ‐butyl peresters, allylic esters, amides, α‐amino nitriles, fully substituted pyrazoles, N ‐sulfonyl formamidines, α‐amino acid esters, cyanomethyl esters, N ‐nitrosamines, and 3‐acyloxy‐2,3‐dihydrobenzofurans have been successfully achieved in high chemoselectivity. Mechanistic studies suggested that TBAI could decompose TBHP to t BuO . and t BuOO . or be oxdized to (hypo)iodite by TBHP.