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.
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.
A transition-metal-free direct carboxylation of the ipso-C(sp2)-H
bond of diazo compounds proceeds at ambient temperature under atmospheric
pressure of carbon dioxide in the presence of a weak base. A series of
unsymmetrical 1,3-diester/keto/amide diazo compounds are obtained with good
yields and good functional group compatibility.
Q. Liu, M. Li, R. Xiong, F. Mo, Org. Lett.,
2017, 19, 6756-6759.
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.
N-Tosyl diazoketamines were prepared by addition of the ethyl
α-diazoacetate anion to N-sulfonylimines. A subsequent diazo decomposition of
the diazoketamines with Rh2(OAc)4 as catalyst provided
α-aryl-β-enamino esters in good yields and high stereoselectivity via aryl
migration.
N. Jiang, Z. Qu, J. Wang, Org. Lett., 2001,
3, 2989-2992.
An improved Arndt-Eistert synthesis to obtain α-diazoketones allows the
efficient transformation of acid halides using a stoichiometric amount of
diazomethane in the presence of calcium oxide, without concomitant ketene or
haloketone formation. The obtained α'-brominated-α-diazoketones were employed
for the synthesis of interesting α-arylamino-α′-halomethylketones.
V. Pace, G. Verniest, J.-V. Sinisterra, A. R. Alcántara, N. De Kimpe, J. Org. Chem., 2010,
75, 5760-5763.
The chain extension of carboxylic acids developed by Arndt and Eistert was
applied to the construction of peptides containing β-amino acids. The method may
be used for the generation of new types of peptide-containing combinatorial
libraries.
J. Podlech, D. Seebach, Angew. Chem. Int. Ed.,
1995, 34, 471-472.
Sonication of diazo ketones derived from Fmoc-protected amino acids in dioxane
in the presence of silver benzoate and water results in clean formation of the
corresponding β-amino acid derivatives. The degree of racemization was examined
using capillary zone electrophoresis. No substantial epimerization occured
except for phenylglycine.
A. Müller, C. Vogt, N. Sewald, Synlett,
2006, 837-841.
