Nothing left to chance: A convenient protocol for selective cross‐coupling of diazo compounds for the convergent synthesis of alkenes was developed (see scheme; EDG=aryl, heteroaryl, vinyl; R=O‐alkyl, aryl). The selectivity control elements were identified by ReactIR and DFT calculations and provide a framework for the design of viable diazo coupling reactions.

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Nothing left to chance: A convenient protocol for selective cross‐coupling of diazo compounds for the convergent synthesis of alkenes was developed (see scheme; EDG=aryl, heteroaryl, vinyl; R=O‐alkyl, aryl). The selectivity control elements were identified by ReactIR and DFT calculations and provide a framework for the design of viable diazo coupling reactions.

Rhodium(II)-Catalyzed Cross-Coupling of Diazo Compounds. -Trisubstituted alkenes are efficiently synthesized by a selective cross-coupling. The reaction is applicable to various aryl and styryl diazo compounds and proceeds with high (E)-selectivity. -(HANSEN, J. H.; PARR, B. T.; PELPHREY, P.; JIN, Q.; AUTSCHBACH, J.; DAVIES*, H. M. L.; Angew.

A combination of donor—acceptor‐substituted rhodium carbenoid catalysts with solvent‐free reaction conditions is used to significantly enhance the turnover numbers (TON) in Rh‐catalyzed C—C bond formation reactions.