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Palladium-catalyzed cross-coupling of ortho -alkenyl bromobenzenes and α-aryl-α-diazoesters was realized. The reactions proceeded in moderate to excellent yields with broad substrate scope, providing a straightforward method for the synthesis of 1,1-disubstituted indenes. The reaction is thought to undergo a tandem alkenyl C–H activation/carbene insertion sequence, in which a C,C-pallada(II)cycle is the key intermediate. [ABSTRACT FROM AUTHOR]