13298-76-5Relevant academic research and scientific papers
A convenient preparation of diazo carbonyl compounds under tri-phase phase-transfer catalysis conditions
Madan Kumar
, p. 2121 - 2127 (1991)
A simple and convenient one-pot preparation method for pure diazo carbonyl compounds under tri-phase phase-transfer catalysis conditions is described.
Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds
Xie, Shibo,Yan, Ziqiang,Li, Yuanheng,Song, Qun,Ma, Mingming
, p. 10916 - 10921 (2018)
We report a crystalline compound 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) as an intrinsically safe, highly efficient, and shelf-stable diazo-transfer reagent. Because the decomposition of ADT is an endothermal process (ΔH = 30.3 kJ mol-1), ADT is intrinsically nonexplosive, as proved by thermal, friction, and impact tests. The diazo-transfer reaction based on ADT gives diazo compounds in excellent yields within several minutes at room temperature. ADT is very stable upon >1 year storage under air at room temperature.
Cobalt(II)-catalyzed asymmetric olefin cyclopropanation with α-ketodiazoacetates
Xu, Xue,Zhu, Shifa,Cui, Xin,Wojtas, Lukasz,Zhang, X. Peter
, (2013)
Porphyrin and Co.: The cobalt(II) complex 1 is an effective metalloradical catalyst for cyclopropanation of alkenes with α-acetodiazoacetates at room temperature to yield E-1,1-cyclopropaneketoesters in high yields with both high diastereo- and enantiosel
Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process
O'Mahony, Rosella M.,Lynch, Denis,Hayes, Hannah L. D.,Ní Thuama, Eilís,Donnellan, Philip,Jones, Roderick C.,Glennon, Brian,Collins, Stuart G.,Maguire, Anita R.
, p. 6533 - 6539 (2017)
The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.
Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation
Zhang, Xueguo,Wang, Peigen,Zhu, Liangwei,Chen, Baohua
, p. 695 - 699 (2021)
Acid-controlled, chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(III)-catalyzed C[sbnd]H activation. Diazo compounds act as a carbene precursor, and coupling occurs in one-pot process, where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.
Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization
Kim, Jiyoung,Yoo, Eun Jeong
, p. 4256 - 4260 (2021)
Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.
Copper-promoted cycloaddition of diazocarbonyl compounds and acetylides
Qi, Xiangbing,Ready, Joseph M.
, p. 3242 - 3244 (2007)
(Chemical Equation Presented) HOMO-logous: The copper-mediated cycloaddition of alkynes with diazo carbonyl compounds to give pyrazoles is reminiscent of the copper-catalyzed cycloaddition of alkynes and azides. The formation of the copper acetylide is proposed to narrow the energy gap between the highest occupied molecular orbital (HOMO) of the alkyne and the lowest unoccupied molecular orbital (LUMO) of the diazo compound.
Construction of enantiomerically enriched diazo compounds using diazo esters as nucleophiles: Chiral Lewis base catalysis
Mao, Haibin,Lin, Aijun,Shi, Yan,Mao, Zhijie,Zhu, Xuebin,Li, Weipeng,Hu, Hongwen,Cheng, Yixiang,Zhu, Chengjian
, p. 6288 - 6292 (2013)
Amazing diazo: The title reaction leads to highly functionalized diazo compounds in good yields with excellent enantioselectivities (see scheme; Boc=tert-butoxycarbonyl). The utility of the products was demonstrated by the rapid synthesis of a number of o
High-load, soluble oligomeric benzenesulfonyl azide: Application to facile diazo-transfer reactions
Harned, Andrew M.,Sherrill, W. Matthew,Flynn, Daniel L.,Hanson, Paul R.
, p. 12093 - 12099 (2005)
The development of a high-load, soluble oligomeric sulfonyl azide using ROM polymerization is reported. The utility in diazo transfer reactions with active methylene compounds is demonstrated using an efficient protocol, with most reactions showing completion in 30 min. The sulfonamide byproduct, being insoluble in the reaction solvent, can be completely removed by simple filtration through a silica gel SPE cartridge.
Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water
Wang, Xiaogang,Zhang, Jin,He, Yuan,Chen, Di,Wang, Chao,Yang, Fangzhou,Wang, Weitao,Ma, Yangmin,Szostak, Michal
, p. 5187 - 5192 (2020)
Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in wate
