Journal
ORGANIC LETTERS
Volume 20, Issue 19, Pages 6112-6116Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02552
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Funding
- National Natural Science Foundation of China [21772137, 21542015, 21672157]
- PAPD
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201708]
- Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions [16KJA150002]
- Soochow University
- State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials
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A regioselective rhodium-catalyzed thiolation of N-tosyl acrylamides with readily available disulfides has been developed. Through N-tosylamide-assisted activation of the alkenyl C(sp(2))-H bond, a series of (Z)-alkenyl sulfides were constructed in moderate to excellent yields with good tolerance of functional groups. Turnover numbers (TONs) of up to 7100 were obtained utilizing 0.01 mol % Rh-III catalyst. In addition, diphenyl diselenide was also successfully applied to this reaction for the construction of (Z)-beta-alkenyl selenides under identical conditions.
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