The direct methylation of ortho C-H bonds in aromatic amides with dicumyl peroxide (DCP) using a nickel complex as the catalyst is reported. The reaction shows a high functional group tolerance and is inhibited by radical scavengers. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bonds.

Diverse ortho-stannylbiaryls and teraryls have been synthesized by copper-catalyzed arylstannylation of arynes, in which the single or dual insertion of arynes into arylstannanes is precisely controllable by simply changing the equivalence of the aryne precursors employed.

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The [4 + 2] cycloaddition of styrenes with arynes was achieved via 1:1 cross-coupling by a nickel catalyst. This protocol applies to a variety of styrenes and arynes generated in situ from o-(trimethylsilyl)aryl triflates to afford 9,10dihydrophenanthrenes involving substituted aromatic rings. By using this method, a naturally occurring stilbenoid is easily synthesized.