Nickel(0)-catalyzed cross-coupling of alkyl arenesulfonates with aryl Grignard reagents
- Authors
- Cho, Chul-Hee; Yun, Hee-Sung; Park, Kwangyong
- Issue Date
- Apr-2003
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.68, no.8, pp 3017 - 3025
- Pages
- 9
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 68
- Number
- 8
- Start Page
- 3017
- End Page
- 3025
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/25001
- DOI
- 10.1021/jo026449n
- ISSN
- 0022-3263
1520-6904
- Abstract
- The nickel-catalyzed cross-coupling reactions of neopentyl arenesulfonates with arylmagnesium bromides, involving nucleophilic aromatic substitution of alkyloxysulfonyl groups by aryl nucleophiles, take place in high yields. Optimal efficiencies are obtained by adding 3 + 2 equiv of the Grignard reagent to a mixture of dppfNiCl(2) and the sulfonate in refluxing THF. Neopentyl arenesulfonates are useful sources of the electrophilic aryl groups in these transition metal-catalyzed cross-coupling reactions. Aryl sulfonates are inappropriate due to their ambident reactivity under the reaction conditions. This new cross-coupling reaction can be used for the creative elimination of alkyloxysulfonyl groups from aromatic compounds and for the preparation of unsymmetric terphenyls and oligophenyls.
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Collections - College of Engineering > School of Chemical Engineering and Material Science > 1. Journal Articles
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