A cobalt-catalyzed decarboxylative cross-coupling reaction of (hetero)aryl carboxylic acids with benzothiazoles or benzoxazoles is reported. This represents a first example of metal-catalyzed decarboxylative C-H heteroarylation of benzo-fused heterocycles. The transformation provides a convenient route, with good yields and functional group tolerance, to various important arylheteroaryl and unsymmetrical biheteroaryl structural motifs.