271-44-3Relevant articles and documents
Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd-Catalyzed Regiodivergent Couplings between Indazoles and Isoprene
Jiang, Wen-Shuang,Ji, Ding-Wei,Zhang, Wei-Song,Zhang, Gong,Min, Xiang-Ting,Hu, Yan-Cheng,Jiang, Xu-Liang,Chen, Qing-An
, p. 8321 - 8328 (2021)
Depending on the reactant property and reaction mechanism, one major regioisomer can be favored in a reaction that involves multiple active sites. Herein, an orthogonal regulation of nucleophilic and electrophilic sites in the regiodivergent hydroamination of isoprene with indazoles is demonstrated. Under Pd-hydride catalysis, the 1,2- or 4,3-insertion pathway with respect to the electrophilic sites on isoprene could be controlled by the choice of ligands. In terms of the nucleophilic sites on indazoles, the reaction occurs at either the N1- or N2-position of indazoles is governed by the acid co-catalysts. Preliminary experimental studies have been performed to rationalize the mechanism and regioselectivity. This study not only contributes a practical tool for selective functionalization of isoprene, but also provides a guide to manipulate the regioselectivity for the N-functionalization of indazoles.
Palladium-catalyzed hydrodefluorination of fluoroarenes
Brodney, Michael A.,Gair, Joseph J.,Giroux, Simon,Grey, Ronald L.
, p. 131 - 146 (2021/06/18)
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A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates
Rekowski, Szymon P.,Kroener, Bettina K.,Kathuria, Deepika,Wani, Aabid A.,Chourasiya, Sumit S.,Conrad, Jürgen,Bharatam, Prasad V.,Frey, Wolfgang,Beifuss, Uwe
, (2021/06/12)
A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.
NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
Lu, Guan-Han,Huang, Tzu-Chia,Hsueh, Hsiao-Chin,Yang, Shin-Cherng,Cho, Ting-Wei,Chou, Ho-Hsuan
supporting information, p. 4839 - 4842 (2021/05/25)
A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).
