期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 36, 页码 8083-8089出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000279
关键词
cross-coupling; cyclization; heterocycles; photochemistry; synthetic methods
资金
- Science and Engineering Research Board [SERB/EMR/2015/002482]
- Council of Scientific and Industrial Research, New Delhi [02(0263)/16/EMR-II]
- UGC, New Delhi
A photocatalyst- and additive-free, visible-light-mediated chemoselective domino protocol was devised to access fully substituted thiazoline derivatives from beta-ketothioamides and alpha-diazo 1,3-diketones at moderate temperature in open air. The reaction proceeds through in situ generation of electrophilic carbenes from alpha-diazo 1,3-diketones by a low-energy blue LED (448 nm), which undergoes selective coupling with nucleophilic beta-ketothioamides to give thiazolines by successive formation of C-S and C-N bonds in one stretch. Notably, the benign and clean conditions, operational simplicity, sustainability, 100 % carbon economy, high yields, and wide functional-group tolerance are further attributes of the strategy. A mechanistic rationale for this cascade reaction sequence is well supported by control experiments.
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