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Amide-Directed Rhodium-Catalyzed Chain-Walking Hydrothiolation of Internal Alkenes
Organic Letters ( IF 5.2 ) Pub Date : 2024-03-18 , DOI: 10.1021/acs.orglett.4c00804
Naoki Hikida 1 , Yasuharu Yoshimi 1 , Hirotsugu Suzuki 2
Affiliation  

We developed a rhodium-catalyzed chain-walking hydrothiolation process for internal alkenes, which offers a novel and efficient alternative for C(sp3)–H bond cleavage, while focusing on thiol incorporation. This method exclusively affords N,S-acetals at 36–90% yields. Regioconvergent hydrothiolation significantly improved the effectiveness of this transformation. Preliminary mechanistic investigations revealed that an amide-directing group is essential for regioselective synthesis, underlining its significance in this process.

中文翻译:

酰胺引导的铑催化内烯烃的链行走硫氢化反应

我们开发了一种用于内部烯烃的铑催化链行走氢硫醇化工艺,该工艺为 C(sp 3 )–H 键断裂提供了一种新颖且有效的替代方案,同时专注于硫醇的掺入。该方法专门提供N , S-缩醛,产率为 36-90%。区域收敛氢硫醇化显着提高了这种转化的有效性。初步的机理研究表明,酰胺导向基团对于区域选择性合成至关重要,强调了其在此过程中的重要性。
更新日期:2024-03-18
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