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Synthesis of Diazo Compounds

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"Activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo compounds at -78C. Under optimized conditions, simple vacuum filtration provides solutions of pure diazo compounds from which stable diazo species can be isolated in high yield, or that can be directly used in subsequent reactions.
M. I. Javed, M. Brewer, Org. Lett., 2007, 9, 1789-1792.


A Bi(V) compound catalyzes an oxidation of hydrazones into diazo compounds in the presence NaBO3H2O as the terminal oxidant. Ph3Bi(OAc)2 as catalyst is in situ generated from BiPh3 and AcOH. The reaction was applied for the synthesis of diazocarbonyls and 2,2,2-trifluoromethyl diazoalkanes in very good yields.
N. Tanbouza, L. Caron, A. Khoshoei, T. Ollevier, Org. Lett., 2022, 24, 2675-2678.


An electrochemical synthesis provides diazo compounds from hydrazones in very high yields and avoids the use of harsh and toxic chemical oxidants. This reaction is practically simple to set up, offers mild conditions, and is highly electron efficient (3 F/mol).
N. Tanbouza, A. Petti, M. C. Leech, L. Caron, J. M. Walsh, K. Lam, T. Ollevier, Org. Lett., 2022, 24, 4665-4663.


"Activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo compounds at -78C. Under optimized conditions, simple vacuum filtration provides solutions of pure diazo compounds from which stable diazo species can be isolated in high yield, or that can be directly used in subsequent reactions.
M. I. Javed, M. Brewer, Org. Lett., 2007, 9, 1789-1792.


The reaction of 1-aryl-2,2,2-trifluorodiazoethanes with alkenes provides trifluoromethyl-substituted cyclopropanes with high diastereoselectivity and enantioselectivity in the presence of an adamantylglycine-derived dirhodium complex Rh2(R-PTAD)4 as catalyst.
J. R. Denton, D. Sukumaran, H. M. L. Davies, Org. Lett., 2007, 9, 2625-2628.