通过双（杂）芳基/烷基-1,3-单硫代二酮和邻溴碘代芳烃的一锅法、铜催化的分子间 C-S 键形成和钯催化的分子内环芳基-烯烃偶联的顺序反应合成取代苯并[b]噻吩。
Synthesis of Substituted Benzo[b]thiophenes via Sequential One-Pot, Copper-Catalyzed Intermolecular C-S Bond Formation and Palladium-Catalyzed Intramolecular Arene-Alkene Coupling of Bis(het)aryl/alkyl-1,3-monothiodiketones and o-Bromoiodoarenes.
机构信息
New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research , Jakkur, Bangalore 560064, India.
出版信息
Org Lett. 2017 Apr 7;19(7):1512-1515. doi: 10.1021/acs.orglett.7b00273. Epub 2017 Mar 16.
A new, convergent, one-pot synthesis of 2,3-substituted benzo[b]thiophenes from readily available 1,3-bis(het)aryl-1,3-monothiodiketones and o-bromoiodoarenes involving a sequential copper-catalyzed intermolecular C-S coupling followed by palladium-catalyzed intramolecular arene-alkene coupling of in situ generated β-(o-bromoaryl)thiovinylketones has been described. Synthesis of a few thieno- and furano-fused 2-(het)aroylethylidenethiochromenes via intramolcular direct C-H (het)arylation of β-(o-bromoaryl)thioenones carrying 2-thienyl/furyl groups under different palladium-catalyzed conditions has also been reported.
一种新的、会聚的、一锅法合成 2,3-取代苯并[b]噻吩的方法，从易得的 1,3-双（杂芳基）-1,3-单硫代二酮和邻溴碘代芳烃出发，涉及顺序铜催化的分子间 C-S 偶联，然后是钯催化的原位生成的β-（邻溴芳基）硫代乙烯基酮的分子内芳基-烯烃偶联。通过在不同钯催化条件下，β-（邻溴芳基）硫代烯酮上带有 2-噻吩基/呋喃基，进行分子内直接 C-H（杂芳基）芳基化反应，合成了几种噻吩并和呋喃并 2-（杂芳基）亚乙基硫代色烯。
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