Reactions of heteroaryllithium compounds with phosphorus trichloride,phosphorus oxychloride,and thionyl chloride. Formation of heterocyclic biaryls

The reactions of four equivalents of heterocyclic aryllithium compounds with phosphorus trichloride or phosphorus oxychloride gave symmetrical heterocyclic biaryls in good yields. A similar coupling was found in the reactions of three equivalents of the lithium compounds with thionyl chloride.