Oxidative Synthesis of 1,3‐Diarylphenanthro[9,10‐c]thiophenes and their Aerobic Photoconversion to 9,10‐Diaroylphenanthrenes

Abstract

AbstractOur study introduces a streamlined oxidative method for synthesizing 1,3‐diarylphenanthro[9,10‐c]thiophenes, and their subsequent oxidative cleavage to yield 9,10‐diaroylphenanthrenes. Harnessing an optimized aerobic photochemical transformation, we showcase broad substrate scope and tolerance to various photosensitive functional groups. Our mechanistic investigations unveil the pivotal role of singlet oxygen, providing intriguing insights into the reaction pathway. The synthesized 9,10‐diaroylphenanthrenes serve as versatile building blocks for nitrogen‐containing heterocycles, dibenzoannulated phthalazines, that are promising compounds with diverse functionalities. Offering mild conditions, and broad applicability, our synthetic strategy is useful for organic synthesis and chemical biology exploration.