Photoredox‐Catalyzed Thiocyanative Cyclization of Biaryl Ynones to Thiocyanated Spiro[5.5]trienones: An External‐Oxidant‐ and Transition‐Metal‐Free Approach

Author:

Samanta Shantanu1,Sarkar Debayan2ORCID

Affiliation:

1. Department of Chemistry National Institute of Technology Rourkela, Odisha 769008 India

2. Department of Chemistry Indian Institute of Technology Indore, Madhya Pradesh 453552 India

Abstract

AbstractA photoredox‐catalyzed, efficient protocol for the direct insertion of a ‐SCN group onto spiro[5.5]trienoneviaa dearomative cascade cyclization of biaryl ynone with inexpensive NH4SCN has been developed, employing 4CzIPN as a potent photocatalyst under blue‐light irradiation without external oxidant. This scalable 6‐exo‐trig cyclization led to the cascade formation of C−C and C−S bonds and incorporate diverse thiocyanated spiro compounds with excellent yield (up to 92 %). Additionally, mechanistic investigations with fluorescence quenching, cyclic voltammetry, and radical scavenging are presented. Gram‐scale synthesis and further functionalization of thiocyanated compounds highlight the potential utility of this methodology.

Funder

National Institute of Technology Rourkela

Indian Institute of Technology Indore

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Analytical Chemistry

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