1422450-72-3Relevant academic research and scientific papers
Cu-Catalyzed Enantioselective Boron Addition to N-Heteroaryl-Substituted Alkenes
Wen, Lu,Yue, Zhenting,Zhang, Haiyan,Chong, Qinglei,Meng, Fanke
, p. 6610 - 6613 (2017)
Catalytic enantioselective Cu-B(pin) (pin = pinacolato) addition to N-heteroaryl-substituted alkenes followed by protonation promoted by phosphine-Cu complexes is presented. The resulting alkylboron products that contain a N-heteroaryl moiety are afforded in up to 97% yield and 99:1 enantiomeric ratio. The highly versatile C-B(pin) bond can be converted to a range of useful functional groups, delivering a variety of enantiomerically enriched building blocks that are otherwise difficult to access. The utility of this method is further demonstrated by application to a fragment synthesis of biologically active molecule U-75302. Preliminary mechanistic studies revealed that the adjacent N atom of the heterocycles plays a unique role in high reactivity and enantioselectivity.
Synthesis of primary and secondary alkylboronates through site-selective C(sp3)-H activation with silica-supported monophosphine-Ir catalysts
Kawamorita, Soichiro,Murakami, Ryo,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 2947 - 2950 (2013/04/10)
The site-selective activation and borylation of unactivated C(sp3)-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located γ to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination.
