Journal
CCS CHEMISTRY
Volume 4, Issue 2, Pages 605-615Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.021.202000760
Keywords
nickel hydride; asymmetric synthesis; radical coupling; reductive hydroalkylation; reductive hydroarylation; enol ester; enol ether
Categories
Funding
- National Natural Science Foundation of China [21732006, 51821006, 21927814, 51961135104]
- Strategic Priority Research Program of CAS [XDB20000000, XDB37040000]
- USTC Research Funds of the Double First-Class Initiative [YD3530002002]
- Users with Excellence Program of Hefei Science Center CAS [2019HSC-UE017, 2019HSC-UE005]
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In this study, a new method for the synthesis of chiral dialkyl carbinols was reported. The cross-coupling reaction between alkyl and aryl with enol esters and ethers was catalyzed by NiH, achieving the formation of C-C bonds with simple operations and a broad substrate scope.
Chiral dialkyl carbinols and their derivatives are significant synthetic building blocks in organic chemistry and related fields. The development of convenient and efficient methods to access these compounds has long been an important endeavor. Herein, we report a NiH-catalyzed reductive hydroalkylation and hydroarylation of enol esters and ethers. alpha-Oxoalkyl organonickel species were generated in situ in a catalytic mode and then participated in cross-coupling with alkyl or aryl halides. This approach enabled C(sp(3))-C(sp(3)) and C(sp(3))-C(sp(2)) bond formation under mild reductive conditions with simple operations, thereby boosting a broad substrate scope and good functional compatibility. Esters of enantioenriched dialkyl carbinols were accessed in a catalytic asymmetric version. Mechanistic studies demonstrated that this reaction proceeded through a syn-addition of Ni-H intermediate to an enol ester with high regio- and enantioselectivity. [GRAPHICS] .
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