The cross-olefination reaction of donor and acceptor diazo compounds was explored. The use of N-nosylhydrazonesas diazo surrogates and the dependence on silver catalysis were crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonate were compatible, and the functionalized alkene products were afforded in good to high yields with moderate (Z)/(E) selectivi-ties. The experimental and DFT calculation results suggest that the cross-selectivity is due to selective activation of the silver catalyst for donor diazo compounds.
