Rhodium(II)‐Catalyzed Cross‐Coupling of Diazo Compounds

2011/02/14 by Jørn H. Hansen, Brendan T. Parr, Philip Pelphrey +3 · 1 citation
Chemistry · #Cyclopropane Reaction Mechanisms #Catalytic C–H Functionalization Methods #Asymmetric Hydrogenation and Catalysis

paper · doi:10.1002/anie.201004923

openalex publication_date 2011/02/14 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

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.

Citations

• Quantum Mechanical Continuum Solvation Models
• Highly stereoselective formation of cis-enediones from α-diazo carbonyl compounds catalysed by [RuCl(η5-C5H5)(PPh3)2]
• Maleates from diazoacetates and dilactones from head-to-head dimerisation of alkenyl diazoacetates using Grubbs' 2nd-generation ruthenium carbene catalyst

Cited by

• Carbene dimerization [wikipedia]

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