- Electrochemical Oxidation Enables Regioselective and Scalable α-C(sp3)-H Acyloxylation of Sulfides
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A highly selective, environmentally friendly, and scalable electrochemical protocol for the construction of α-acyloxy sulfides, through the synergistic effect of self-assembly-induced C(sp3)-H/O-H cross-coupling, is reported. It features exceptionally broad substrate scope, high regioselectivity, gram-scale synthesis, construction of complex molecules, and applicability to a variety of nucleophiles. Moreover, the soft X-ray absorption technique and a series of control experiments have been utilized to demonstrate the pivotal role of the self-assembly of the substrates, which indeed is responsible for the excellent compatibility and precise control of high regioselectivity in our electrochemical protocol.
- Wang, Huamin,He, Meng,Li, Yongli,Zhang, Heng,Yang, Dali,Nagasaka, Masanari,Lv, Zongchao,Guan, Zhipeng,Cao, Yangmin,Gong, Fengping,Zhou, Zhilin,Zhu, Jingyun,Samanta, Supravat,Chowdhury, Abhishek Dutta,Lei, Aiwen
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supporting information
p. 3628 - 3637
(2021/04/07)
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- Fe2O3-catalyzed Pummerer rearrangement of acyl chlorides and sulfoxides: Facile synthesis of alkylthiomethyl ester
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A simple, effective approach for the Pummerer rearrangement of acyl chlorides with sulfoxides by using a low-cost and more abundant Fe catalyst has been described. The alkylthiomethyl ester products were prepared in good to excellent yields for a range of different substrates including asymmetrical sulfoxides and acyl chlorides with a variety of functional groups under mild reaction conditions. The reaction features short reaction time, simple manipulation, cheap reagents and a broad substrate scope. Single crystal X-ray analysis of a representative methylthiomethyl (MTM) group containing product was also reported.
- Xing, Haotian,Chen, Long,Jia, Yimin,Jiang, Zhongxing,Yang, Zhigang
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supporting information
p. 2199 - 2202
(2017/05/16)
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- Method for preparing alkylthiomethyl ester compounds
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The invention discloses a method for preparing alkylthiomethyl ester compounds and belongs to the field of organic chemistry. The method disclosed by the invention comprises the following steps: dissolving sulfoxide, an iron salt reagent and an alkali in a non-protonic solvent under inert gas shielding; adding an acyl chloride reagent into the system, stirring and reacting to enable alpha-carbon rearranged by sulfoxide molecules to combine with acyloxy transformed by acyl chloride molecules, thereby obtaining the alkylthiomethyl ester. The method disclosed by the invention is simple in reaction, mild in conditions, low in cost and wide in application range; and the reaction product can become an important and effective carboxyl protecting group, and the absorption effect of certain drugs can be improved.
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Paragraph 0041; 0042
(2017/08/31)
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