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Development and Mechanistic Studies of (<i>E</i>)-Selective Isomerization/Tandem Hydroarylation Reactions of Alkenes with a Nickel(0)/Phosphine Catalyst
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- Hiroaki Iwamoto
- Department of Applied Chemistry, Osaka University, Suita, Osaka 565-0871, Japan
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- Takuya Tsuruta
- Department of Applied Chemistry, Osaka University, Suita, Osaka 565-0871, Japan
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- Sensuke Ogoshi
- Department of Applied Chemistry, Osaka University, Suita, Osaka 565-0871, Japan
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Description
A stereoselective alkene isomerization and sequential hydroarylation with arylboronic acid using a nickel(0) catalyst has been developed. The bulky monophosphine PAd 2 ( n -Bu) is an effective ligand in these reactions to furnish both various stereo-defined internal alkenes and hydroarylation products (isomerization: up to 98%, E / Z = 98:2; tandem hydroarylation: up to 82%). Mechanistic studies based on experiments and computational calculations suggested that the isomerization proceeds via an intra- or intermolecular hydrogen shift. Furthermore, a concerted multibond recombination with boronic acid-assisted oxidative protometallation of the alkene was found to be a reasonable mechanism for the formation of the alkylnickel(II) species from the alkene, nickel(0), alcohol, and boronic acid in the hydroarylation.
Journal
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- ACS Catalysis
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ACS Catalysis 11 (11), 6741-6749, 2021-05-26
American Chemical Society (ACS)
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Keywords
- Chemical Sciences not elsewhere classified
- boronic acid
- Biophysics
- sequential hydroarylation
- Biochemistry
- hydrogen shift
- multibond recombination
- Environmental Sciences not elsewhere classified
- Genetics
- Molecular Biology
- Computational Biology
- monophosphine PAd 2
- isomerization proceeds
- Cell Biology
- arylboronic acid
- hydroarylation products
- stereoselective alkene isomerization
- Infectious Diseases
- boronic acid-assisted oxidative pro.
- Mechanistic Studies
- Medicine
- Biotechnology
- Developmental Biology
- Biological Sciences not elsewhere classified
Details 詳細情報について
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- CRID
- 1360294643836384384
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- ISSN
- 21555435
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- Article Type
- journal article
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- Data Source
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- Crossref
- KAKEN
- OpenAIRE
