Selenosulfonation of 1,3-dienes: One-pot synthesis of 2-(phenylsulfonyl)-1,3-dienes

✍ Scribed by Jan-E. Bäckvall; Carmen Nájera; Miguel Yus

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 228 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)80320-2

✦ Synopsis

A one-pot procedure for the transformation of a 1,3-diene into the corresponding 2-(phenylsulfonyl)-1,3-diene was developed. The reaction involves a 1,2-selenosulfonation-oxidation sequence. 2-( Phenylsulfonyl)-1,3-dienes have recently been shown to be versatile synthons in organic transformations. 2-5 They can be used as multicoupling reagents and as Diels-Alder dienes with a dual electron demand. 3 In addition, regioselective epoxidation of either double bond leads to synthetically useful epoxy sulfones. 4 The previous procedure for the synthesis of 2-(phenylsulfonyl)-1,3-dienes from 1,3-dienes was based on a 1,2-sulfonylmercuration-elimination sequence. A drawback with this procedure is that it involves the use of mercury. Because of the increasing importance of these sulfonyldienes, alternative methods 6 for their preparation seemed highly desirable. In this communication we report a one-pot procedure for the preparation of 2-(phenylsulfonyl)-1,3-dienes that is based on a selenosulfonation-oxidation7 sequence (eq. 1).