Journal
ACS CATALYSIS
Volume 13, Issue 7, Pages 4409-4420Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.3c00238
Keywords
nickel; hydrofunctionalization; hydroamination; hydroetherification; chain-walking
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This research presents an efficient nickel-catalyzed remote hydroamination and hydroetherification method, which allows the installation of amino or alkoxyl groups at C(sp3)-H positions that are far from the double bond of alkenes. The yields are as high as 93% with exclusive regioselectivities.
Transition metal-catalyzed remote hydrofunctional-ization of alkenes is an efficient method to realize C(sp3)-H functionalization. However, remote hydrofunctionalization of alkenes with unactivated amines and alcohols has not been successfully developed to date. Herein, we report an efficient nickel-catalyzed remote hydroamination and hydroetherification of alkenes with unactivated amines and alcohols, accessing a series of gem-diamine and N,O-acetal derivatives in good to high yields (up to 93%) and exclusive regioselectivities. The mechanistic investigations and DFT computations indicated that the use of 2-iodo-2-methylpropane (tBuI) as both a mild hydride source and radical precursor was essential to afford the remote functionalized products. This research work provides an efficient method to install an amino or alkoxyl at the C(sp3)-H position that is far from the double bond of alkenes.
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