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

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.

Catalytic cross-coupling of diazo compounds with coinage metal-based catalysts: an experimental and theoretical study

“…4 Hodgson and co-workers described 5 the crosscoupling of two diazoacetates of formulae N 2 C(H)CO 2 R with different R groups. But it was not until very recently that Davies and co-workers have described a rhodium-based catalytic system to promote the efficient cross-coupling of two distinct diazo compounds 6 with a very high regioselectivity toward the E isomer [eqn (1)]. We have described several catalytic systems based on the group 11 metal complexes for the addition 7 …”

A Convergent Synthesis of Gonytolide C Using an Intramolecular Oxa‐Michael Addition

“…We noted that 1,3-diacetoxyacetone (16), an easily obtainable stable solid, [18] has been used previously as a substrate for both HWE and Wittig-type reactions. [19,20] Elaboration of the acetateprotected diol to both a γ-butyrolactone and a methyl ester, at a later stage as required for the natural product, also appeared possible.…”

Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity

“…Their remarkable selectivity has reached a stage where they can function as a powerful tool in building up value added molecules with complex structures [7,[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34].…”