Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 36, Pages 15512-15516Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202002936
Keywords
alkenyl sulfides; benziodoxolones; hypervalent compounds; synthetic methods; vinylbenziodoxolones
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Funding
- Carl Trygger Foundation [CTS 17:341]
- Swedish Research Council [2015-04404]
- Swedish Research Council [2015-04404] Funding Source: Swedish Research Council
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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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