The chemistry of organolead(IV) tricarboxylates. Synthesis and electrophilic heteroarylation reactions of 2- and 3-thienyl-, and 2- and 3-furyl-lead tricarboxylates

Abstract

Tin(IV)–lead(IV) exchange and mercury(II)–lead(IV) exchange reactions have been used to obtain 2-thienyl-lead triacetate (3), 2-thienyl-lead tribenzoate (4), 3-thienyl-lead triacetate (16), 2-furyl-lead triacetate (21), and 3-furyl-lead triacetate (31). In reactions with the β-dicarbonyl compounds (7), (11), and (13), the above heteroaryl-lead compounds behaved as 2-thienyl, 3-thienyl, 2-furyl, and 3-furyl cation equivalents respectively, giving the α-heteroaryl β-dicarbonyl compounds (8), (12), (14), (17), (18), (19), (25), (27), (28), (33), (34), and (35) in synthetically useful yields.