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The central aim is to develop a new synthetic route for 1,2-bis(indolyl)ethenes and benzo[α]carbazoles using vinylene carbonate.

January 23, 2026Organic Letters0 citations

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Vinylene Carbonate as an Ethylene Equivalent for the Synthesis of 1,2-Bis(indolyl)ethenes and Benzoαcarbazoles

JHJiheun Hyun KMKyeongwon Moon JJJimin Jeong

Key Points

The central aim is to develop a new synthetic route for 1,2-bis(indolyl)ethenes and benzo[α]carbazoles using vinylene carbonate.
Synthesis of acetal intermediate from vinylene carbonate and HFIP
Electrophilic substitution to generate indolyl-3-acetaldehydes
Condensation of indolyl-3-acetaldehydes with additional indoles or C2-aryl rings
Produced 1,2-bis(indolyl)ethenes and benzo[α]carbazoles through the described mechanism
Demonstrated the feasibility of using vinylene carbonate as an ethylene equivalent

Abstract

An unprecedented strategy for synthesizing 1,2-bis(indolyl)ethenes and benzoαcarbazoles is described herein. Mechanistically, an acetal intermediate, derived from vinylene carbonate and HFIP, is involved in electrophilic substitution to free (NH)-indoles, generating indolyl-3-acetaldehydes. Subsequent electrophilic condensation between these indolyl-3-acetaldehydes and additional indoles or C2-aryl rings affords (E)-1,2-bis(indolyl)ethenes and benzoαcarbazoles, respectively.

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Vinylene Carbonate as an Ethylene Equivalent for the Synthesis of 1,2-Bis(indolyl)ethenes and Benzoαcarbazoles

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