C–H Arylation of N‐Heteroarenes under Metal‐Free Conditions and its Application towards the Synthesis of Pentabromo‐ and Pentachloropseudilins

Herein, we are reporting metal‐free conditions for radical initiation and direct C–H arylation of N‐heteroarenes. Starting from aniline, the corresponding arenediazonium salt generated in situ is reduced to an aryl radical in the presence of chloropromazine hydrochloride, a new reagent for this application. The optimized procedures are mild, operationally simple, and are working successfully with more diverse substrates in comparison to reported methods. The optimized method is also employed for the synthesis of marine natural products Pentabromo‐ and Pentachloropseudilins (PBP/PCP). In the present study, we also validated the potential of the Pentachloropseudilin (PCP), thus synthesized, for inhibition of Myosin1 function in mammalian cells and confirmed that PCP phenocopies Myosin1c depletion in cells. Herein, we have developed a metal‐free and mild condition for the synthesis of 2‐arylated heteroarenes. The complex forming property and charge transfer property of phenothiazine expanded its application towards catalysis The optimized condition has been successfully employed for the synthesis important marine natural product namely pentabromo/chloropseudilins (PBP/PCP). The synthesized Pentachloropseudilin (PCP) has been shown to phenocopy the effect of Myosin1c depletion which provides a strong justification for the use of PCP as a specific probe for Myosin 1 function in cells.