1181219-07-7Relevant articles and documents
Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
Chang, Xiao-Yong,Chen, Ji-Jun,Gu, Qiang-Shuai,Jiang, Sheng-Peng,Li, Zhong-Liang,Liu, Lin,Liu, Xiao-Dong,Liu, Xin-Yuan,Su, Xiao-Long,Wang, Fu-Li,Yang, Chang-Jiang,Ye, Liu
, p. 380 - 384 (2021)
The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
Nickel-catalyzed C-H alkenylation and alkylation of 1,3,4-oxadiazoles with alkynes and styrenes
Mukai, Tomoya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information; experimental part, p. 6410 - 6413 (2009/12/06)
(Chemical Equation Presented) The addition reaction of 1,3,4-oxadiazoles to alkynes via C-H bond cleavage efficiently proceeds in the presence of a nickel catalyst. This direct coupling allows a facile access to alkenyl-substituted oxadiazoles. The reaction with styrenes in place of alkynes is also available to selectively afford the corresponding branched adducts.