- Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides
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A palladium-catalyzed α-arylation of sulfonamides with aryl chlorides is presented. A Buchwald-type pre-catalyst formed with Kwong’s indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines. (Figure presented.) .
- Zheng, Bing,Li, Minyan,Gao, Gui,He, Yuying,Walsh, Patrick J.
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supporting information
p. 2156 - 2162
(2016/07/16)
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- Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite
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Starting from alkyl halides or Michael acceptors, thioacetates were prepared in situ and further treated with t-BuOCl, affording the corresponding sulfonyl chlorides which were trapped with nucleophiles such as water, alcohol, or amines. The three steps can be achieved in a one-pot procedure. Oxidative deprotection also proved to be efficient with S-trityl and S-tert-butyl groups, making it a convenient route toward cysteic acid derivatives.
- Joyard, Yoann,Papamicael, Cyril,Bohn, Pierre,Bischoff, Laurent
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supporting information
p. 2294 - 2297
(2013/06/05)
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- DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation
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The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.
- Woolven, Holly,Gonzalez-Rodriguez, Carlos,Marco, Isabel,Thompson, Amber L.,Willis, Michael C.
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p. 4876 - 4878
(2011/12/05)
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