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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

Combination of Tetrabutylammonium Iodide (TBAI) With tert-Butyl Hydroperoxide (TBHP): An Efficient Transition-Metal-Free System to Construct Various Chemical Bonds

Rongxiang Chen, Jijun Chen, Jie Zhang, Xiaobing Wan

Chem Rec. 2018 Sep;18(9):1292-1305.

PMID: 29513383

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP311284	Tetrabutylammonium iodide		311-28-4	Price

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