Organic Chemistry Portal
Reactions > Organic Synthesis Search

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

Synthesis of Diazo Compounds

Related:


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.


A safe and fast method for the production of β-hydroxy-α-diazoesters involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. In a three-step sequence, Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters.
S. T. R. Müller, D. Smith, P. Hellier, T. Wirth, Synlett, 2014, 25, 871-875


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.