Base-mediated alternate route for multi-functionalized allylbenzenes using ring transformation strategy

Abstract

A simple yet innovative approach for the construction of multi-substituted allylbenzenes 14, 16 and 18 with ‘donor-acceptor’ functionalities has been delineated through base-mediated ring transformation of 6-aryl-2H-pyran-2-ones 13, 15 and 17 respectively with commercially available 5-hexen-2-one 11 as carbanion source. The reactions were carried out at room temperature without using any catalyst or organometallic reagents with excellent functional group tolerance. Moreover, the present method is possible alternate route to access allylbenzenes apart from usual metal-catalyzed cross-coupling reactions.

Graphical Abstract

Keywords:

• Allylbenzene
• 5-hexen-2-one
• 2H-pyran-2-ones
• ring transformation
• secondary amines

Acknowledgments

We thank the SAIF department, VIT Vellore for spectrometric data. Fateh V. Singh is thankful to VIT Chennai for providing seed grant to do this research work.

Additional information

Funding

Authors are thankful to VIT Chennai for providing financial assistance.