777-22-0Relevant articles and documents
Iron(II)-Catalyzed Site-Selective Functionalization of Unactivated C(sp3)?H Bonds Guided by Alkoxyl Radicals
Guan, Honghao,Sun, Shutao,Mao, Ying,Chen, Lei,Lu, Ran,Huang, Jiancheng,Liu, Lei
supporting information, p. 11413 - 11417 (2018/08/28)
An alkoxyl radical guided strategy for site-selective functionalization of unactivated methylene and methine C?H bonds enabled by an FeII-catalyzed redox process is described. The mild, expeditious, and modular protocol allows efficient remote aliphatic fluorination, chlorination, amination, and alkynylation of structurally and electronically varied primary, secondary, and tertiary hydroperoxides with excellent functional-group tolerance. The application for one-pot 1,4-hydroxyl functionalization of non-oxygenated alkane substrates initiated by aerobic C?H oxygenation is also demonstrated.
Electron-Transfer and Hydride-Transfer Pathways in the Stoltz–Grubbs Reducing System (KOtBu/Et3SiH)
Smith, Andrew J.,Young, Allan,Rohrbach, Simon,O'Connor, Erin F.,Allison, Mark,Wang, Hong-Shuang,Poole, Darren L.,Tuttle, Tell,Murphy, John A.
, p. 13747 - 13751 (2017/10/12)
Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert-butoxide react to form a highly attractive and versatile system that shows (reversible) silylation of arenes and heteroarenes as well as reductive cleavage of C?O bonds in aryl ethers and C?S bonds in aryl thioethers. Their extensive mechanistic studies indicate a complex network of reactions with a number of possible intermediates and mechanisms, but their reactions likely feature silyl radicals undergoing addition reactions and SH2 reactions. This paper focuses on the same system, but through computational and experimental studies, reports complementary facets of its chemistry based on a) single-electron transfer (SET), and b) hydride delivery reactions to arenes.
Silver-catalyzed cross-coupling reactions of alkyl bromides with alkyl or aryl Grignard reagents
Someya, Hidenori,Yorimitsu, Hideki,Oshima, Koichiro
supporting information; experimental part, p. 3270 - 3272 (2009/08/09)
Treatment of secondary or tertiary alkyl bromides with alkyl Grignard reagents in the presence of catalytic amounts of silver bromide and potassium fluoride in CH2Cl2 afforded the corresponding cross-coupling products in reasonable yields. Moreover, silver showed catalytic activity for the cross-coupling reactions of alkyl bromides with aryl Grignard reagents.
