1233731-18-4Relevant academic research and scientific papers
Transition-metal-free multinitrogenation of amides by C-C bond cleavage: A new approach to tetrazoles
Li, Lian-Hua,Li, Ying-Xiu,Liang, Yong-Min,Niu, Zhi-Jie
supporting information, p. 11148 - 11151 (2020/04/22)
A metal-free brand-new one-pot multinitrogenation of amides for the chemo- A nd regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C-C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives were selectively constructed under mild conditions. As showcased in the mechanisms, the chemoselectivity is easily switched by the selection of the starting materials in the reaction.
Modular radical cross-coupling with sulfones enables access to sp3-rich (fluoro)alkylated scaffolds
Merchant, Rohan R.,Edwards, Jacob T.,Qin, Tian,Kruszyk, Monika M.,Bi, Cheng,Che, Guanda,Bao, Deng-Hui,Qiao, Wenhua,Sun, Lijie,Collins, Michael R.,Fadeyi, Olugbeminiyi O.,Gallego, Gary M.,Mousseau, James J.,Nuhant, Philippe,Baran, Phil S.
, p. 75 - 80 (2018/02/28)
Cross-coupling chemistry is widely applied to carbon-carbon bond formation in the synthesis of medicines, agrochemicals, and other functional materials. Recently, single-electron-induced variants of this reaction class have proven particularly useful in the formation of C(sp2)-C(sp3) linkages, although certain compound classes have remained a challenge. Here, we report the use of sulfones to activate the alkyl coupling partner in nickel-catalyzed radical cross-coupling with aryl zinc reagents. This method's tolerance of fluoroalkyl substituents proved particularly advantageous for the streamlined preparation of pharmaceutically oriented fluorinated scaffolds that previously required multiple steps, toxic reagents, and nonmodular retrosynthetic blueprints. Five specific sulfone reagents facilitate the rapid assembly of a vast set of compounds, many of which contain challenging fluorination patterns.
Synthesis of 1,5-disubstituted tetrazoles via Suzuki-Miyaura cross-coupling of 5-chloro-1-phenyltetrazole
Tang, Qing,Gianatassio, Ryan
experimental part, p. 3473 - 3476 (2010/08/20)
Suzuki-Miyaura coupling reactions of 5-chloro-1-phenyl-tetrazole with various functionalized arylboronic acids were investigated. In the presence of catalytic amounts of SPhos/Pd(OAc)2 or RuPhos/Pd(OAc)2, the reaction proceeded smoot
