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Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-12 00:00:00 , DOI: 10.1039/c7ob01605k Yulia A. Konik 1, 2, 3, 4 , Gábor Zoltán Elek 5, 6, 7, 8 , Sandra Kaabel 5, 6, 7, 8 , Ivar Järving 5, 6, 7, 8 , Margus Lopp 5, 6, 7, 8 , Dzmitry G. Kananovich 5, 6, 7, 8
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-12 00:00:00 , DOI: 10.1039/c7ob01605k Yulia A. Konik 1, 2, 3, 4 , Gábor Zoltán Elek 5, 6, 7, 8 , Sandra Kaabel 5, 6, 7, 8 , Ivar Järving 5, 6, 7, 8 , Margus Lopp 5, 6, 7, 8 , Dzmitry G. Kananovich 5, 6, 7, 8
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Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of a copper(II) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluoroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones in up to 94% yields. The experimental protocol is mild and tolerates a number of functionalities in the cyclopropanol substrate. The reaction proceeds via a one-pot oxidation–Michael addition mechanism and can serve as a useful addition to the existing methods for the preparation of γ-keto sulfones based on the sulfa-Michael reaction.
中文翻译：
铜催化叔环丙醇的氧化磺化反应合成γ-酮砜
当在乙酸铜（II）催化剂和氧化剂（叔丁基氢过氧化物或大气氧）存在下与亚磺酸盐反应时，叔环丙醇进行开环氧化磺酰化，得到γ-酮砜。各种氟烷基，芳基和烷基亚磺酸盐已成功地用作磺酰化试剂，以高达94％的收率提供了相应的砜。实验规程温和，可耐受环丙醇底物中的许多功能。该反应通过一锅氧化-迈克尔加成机理进行，可作为基于磺胺-迈克尔反应制备γ-酮砜的现有方法的有用补充。
更新日期：2017-09-22
中文翻译：
铜催化叔环丙醇的氧化磺化反应合成γ-酮砜
当在乙酸铜（II）催化剂和氧化剂（叔丁基氢过氧化物或大气氧）存在下与亚磺酸盐反应时，叔环丙醇进行开环氧化磺酰化，得到γ-酮砜。各种氟烷基，芳基和烷基亚磺酸盐已成功地用作磺酰化试剂，以高达94％的收率提供了相应的砜。实验规程温和，可耐受环丙醇底物中的许多功能。该反应通过一锅氧化-迈克尔加成机理进行，可作为基于磺胺-迈克尔反应制备γ-酮砜的现有方法的有用补充。
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