Direct Synthesis of Allylic Thioethers Under Greener Conditions: A Solvent- and Catalyst-Free Approach

Abstract

We present herein a new catalyst-free and solvent-free approach for the synthesis of allylic thioethers directly from allylic alcohols and thiols. The methodology allows the synthesis of different allylic thioethers in good to excellent yields under microwave irradiation. Theoretical calculations for the allylic carbocation helped to explain the regioselectivity observed when nonsymmetric substrates are used in the reaction.

GRAPHICAL ABSTRACT

Keywords:

• Allylic thioethers
• catalyst-free
• green chemistry
• solvent-free

Notes

^a Reaction conditions: (E)-1,3-Diphenylprop-2-en-1-ol 1a (0.5 mmol), benzenethiol 2a (0.6 mmol).

^b Isolated yields.

^c 4 mmol of benzenethiol 2a was used.

^d Conventional heating.

^a Reaction conditions: (E)-1,3-Diphenylprop-2-en-1-ol 1a (0.5 mmol), thiol 2 (0.6 mmol).

^b Isolated yields.

^a Reaction conditions: Allylic alcohol (0.5 mmol), thiol 2a (0.6 mmol).

^b Isolated yields.

^c Regioisomeric ratio was determined based on NMR data.

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