期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 38, 页码 10204-10208出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404527
关键词
alcohols; arenes; palladium; sulfonamides; synthetic methods
资金
- EPSRC
- AstraZeneca
- EPSRC [EP/K00803X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K00803X/1] Funding Source: researchfish
Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas-and reductant-free reaction include the low loadings of palladium (1 mol%) and ligand (1.5 mol%) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.
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