期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 36, 页码 15512-15516出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202002936
关键词
alkenyl sulfides; benziodoxolones; hypervalent compounds; synthetic methods; vinylbenziodoxolones
资金
- Carl Trygger Foundation [CTS 17:341]
- Swedish Research Council [2015-04404]
- Swedish Research Council [2015-04404] Funding Source: Swedish Research Council
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
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