Fast Heating-Assisted One-Pot Copper-Catalyzed Sulfonylation and Sulfochlorination of Styrenes

被引:7
|
作者
Saavedra-Olavarria, Jorge [1 ]
Hermosilla-Ibanez, Patricio [2 ]
Almodovar, Iriux [3 ]
Perez, Edwin G. [4 ]
机构
[1] Univ Chile, Fac Sci, Dept Chem, Las Palmeras 3425, Santiago 7800003, Chile
[2] Univ Santiago, Ctr Dev Nanosci & Nanotechnol CEDENNA, Mat Chem Dept, Fac Chem & Biol, Santiago, Chile
[3] Univ Santiago Chile, USACh, Faulty Chem & Biol, Ave Libertador Bernardo OHiggins 3363, Santiago, Chile
[4] Pontificia Univ Catolica Chile, Fac Chem & Pharm, Dept Organ Chem, Vicuna Mackenna 4860, Santiago 7820436, Chile
关键词
Catalysis; Copper; One pot synthesis; Sulfochlorination; Sulfonylation; VINYL SULFONES; METAL-FREE; STEREOSELECTIVE-SYNTHESIS; SELECTIVE SYNTHESIS; ALKYNES; ALKENES; IODINE; FUNCTIONALIZATION; CHEMISTRY; AGENTS;
D O I
10.1002/ejoc.202101526
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, a strategy for the synthesis under fast-heating conditions of vinyl sulfones and beta-chlorosulfones from styrene derivatives, tosyl chloride (TsCl) as sulfonyl and chlorine source, and CuBr-neocuproine as the catalytic system is reported. The reaction occurs through an atom transfer radical addition (ATRA) mechanism to generate the sulfochlorinated adducts followed by E2 elimination to generate the vinyl sulfones. This methodology allows a wide range of vinyl sulfones and beta-chlorosulfones to be obtained using inexpensive reagents in one and five minutes respectively. These reactions appear as an interesting fast and easy-to-handle alternative to obtain these compounds.
引用
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页数:5
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