Journal
ACS CATALYSIS
Volume 12, Issue 12, Pages 7262-7268Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c01697
Keywords
alkenes; alkylarylation; C(sp3)-C(sp3); imines; nickel-catalyzed; stereoselective
Categories
Funding
- NIH NIGMS [R35GM133438]
- Pennsylvania State University (Penn State)
- NSF-MRI program [CHE-2018870]
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We have disclosed a novel Ni-catalyzed alkylarylation reaction of electron-deficient alkenes, which allows the construction of two carbon-carbon bonds. The electron-deficient alkenes play a crucial role in stabilizing reaction intermediates and enhancing the catalytic rates. This reaction is also applicable to secondary alkylzinc reagents and internal alkenes, and exhibits excellent regio- and stereocontrol, leading to products with up to three contiguous all-carbon all-cis secondary stereocenters.
We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in y,(5-alkenylketimines with aryl halides and arylketones with the construction of two C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp3)-C(sp3) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.
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