Journal
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
Volume 74, Issue 11, Pages 1119-1127Publisher
SOC SYNTHETIC ORGANIC CHEM JPN
DOI: 10.5059/yukigoseikyokaishi.74.1119
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Funding
- JSPS KAKENHI Grant [JP25107002, JP24685007, JP26620081, JP16H01019, JP16H01149, JP16H04109]
- ACT-C, JST
- Japan Association for Chemical Innovation
- Naito Foundation
- Tokuyama Science Foundation
- Kyoto University Research Fund for Young Scientists
- JSPS
- Grants-in-Aid for Scientific Research [24685007, 16H01149, 25107002, 14F04335, 16H01019] Funding Source: KAKEN
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Cross-coupling reactions of aryl sulfides are more difficult than they look. We have disclosed that transition metal-NHC complexes allow us to efficiently use a wide range of aryl sulfides as electrophilic coupling partners in various cross-coupling reactions and have thus significantly expanded the scope of aryl sulfides available for the cross-coupling technology. Newly introduced nucleophilic partners include arylzinc reagents, Grignard reagents such as alkynylmagnesium species, amines, ketimines, and diborons to achieve Negishi-type coupling, Kumada-Tamao-Corriu-type coupling, Buchwald-Hartwig-type amination, Buchwald-Hartwig-Miura-type carbonyl alpha-arylation, and Miyaura-type borylation, respectively. These cross-coupling reactions are particularly advantageous when combined with sulfur-specific transformations to prepare organosulfur substrates. Through the development of catalytic transformations of C-S bonds, sulfur based organic synthesis has come to complement conventional halogen-based organic methodology.
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