27262-63-1Relevant articles and documents
Intermolecular [5 + 1]-Cycloaddition between Vinyl Diazo Compounds and tert-Butyl Nitrite to 1,2,3-Triazine 1-Oxides and Their Further Transformation to Isoxazoles
De Angelis, Luca,Zheng, Haifeng,Perz, Matthew T.,Arman, Hadi,Doyle, Michael P.
supporting information, p. 6542 - 6546 (2021/08/30)
1,2,3-Triazine 1-oxides are formed by nitrosyl addition from tert-butyl nitrite to the vinylogous position of vinyl diazo compounds. This transformation, which is a formal intermolecular [5 + 1] cycloaddition, occurs under mild conditions, with high funct
Ethyl Lithiodiazoacetate: Extremely Unstable Intermediate Handled Efficiently in Flow
Müller, Simon T. R.,Hokamp, Tobias,Ehrmann, Svenja,Hellier, Paul,Wirth, Thomas
supporting information, p. 11940 - 11942 (2016/08/16)
Ethyl diazoacetate (EDA) is one of the most prominent diazo reagents. It is frequently used in metal–carbene-type reactions. However, EDA can also be used as a nucleophile under base catalysis. Whilst the addition of EDA to aldehydes can be performed using organic bases, the addition of EDA to other carbonyl electrophiles requires the use of organometallics such as lithium diisopropylamide (LDA). The generated ethyl lithiodiazoacetate is highly reactive and decomposes rapidly, even at low temperatures. Herein, we report a continuous flow protocol that overcomes the problems associated with the instantaneous decomposition of ethyl lithiodiazoacetate. The addition of ethyl lithiodiazoacetate to ketones provides direct access to tertiary diazoalcohols in good yields.
Pd-catalyzed coupling of β-hydroxy α-diazocarbonyl compounds with aryl iodides: A migratory insertion/β-hydroxy elimination sequence
Zhou, Lei,Liu, Yizhou,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 3622 - 3624 (2011/05/02)
The coupling of β-hydroxy α-diazocarbonyl compounds with aryl halides is described, which proceeds through a Pd-catalyzed migratory insertion/β-OH elimination sequence. This reaction provides a new route to the synthesis of tetrasubstituted olefins.