Categories: C-C Bond Formation > Nitrogen-containing molecules >

Synthesis of Diazo Compounds

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Recent Literature

The Pd-catalyzed reaction between aryl or vinyl iodides and ethyl diazoacetate (EDA) provides cross-coupling products in good yields.
C. Peng, J. Cheng, J. Wang, J. Am. Chem. Soc., 2007, 129, 8708-8709.

C. Peng, J. Cheng, J. Wang, J. Am. Chem. Soc., 2007, 129, 8708-8709.

C. Peng, J. Cheng, J. Wang, J. Am. Chem. Soc., 2007, 129, 8708-8709.

Silica-supported tetramethylguanidine catalyst was prepared and effectively used in the aldol-type coupling of aldehydes with ethyl diazoacetate to afford the corresponding α-diazo-β-hydroxy esters in very good yields. The catalyst can be reused for a number of cycles with almost consistent activity by a simple filtration.
P. R. Likhar, S. Roy, M. Roy, M. S. Subhas, M. Lakshmi Kantam, Synlett, 2008, 1283-1286.

The reaction of diazo(trimethylsilyl)methylmagnesium bromide with aldehydes or ketones gave 2-diazo-2-(trimethylsilyl)ethanols, which were applied to the synthesis of di- and trisubstituted pyrazoles via [3+2] cycloaddition reaction with ethyl propiolate or dimethyl acetylenedicarboxylate.
Y. Hari, S. Tsuchida, R. Sone, T. Aoyama, Synthesis, 2007, 3371-3375.

An axially chiral dicarboxylic acid has been applied to a highly enantioselective Mannich reaction of arylaldehyde N-Boc imines and diazo compounds as a new class of chiral hydrogen-bonding catalyst.
T. Hashimoto, K. Maruoka, J. Am. Chem. Soc., 2007, 129, 10054-10055.