10412-65-4Relevant articles and documents
Site-selective aliphatic C-H bromination using N -bromoamides and visible light
Schmidt, Valerie A.,Quinn, Ryan K.,Brusoe, Andrew T.,Alexanian, Erik J.
supporting information, p. 14389 - 14392 (2014/12/10)
Transformations that selectively functionalize aliphatic C-H bonds hold significant promise to streamline complex molecule synthesis. Despite the potential for site-selective C-H functionalization, few intermolecular processes of preparative value exist. Herein, we report an approach to unactivated, aliphatic C-H bromination using readily available N-bromoamide reagents and visible light. These halogenations proceed in useful chemical yields, with substrate as the limiting reagent. The site selectivities of these radical-mediated C-H functionalizations are comparable (or superior) to the most selective intermolecular C-H functionalizations known. With the broad utility of alkyl bromides as synthetic intermediates, this convenient approach will find general use in chemical synthesis.
Stereoselectivity of Radical Additions of N-Haloimides to Cyclic Alkenes
Kirsch, Andre,Luening, Ulrich,Krueger, Oliver
, p. 649 - 656 (2007/10/03)
The addition of N-haloimides (1-5) to alkenes 9 via imidyl radicals 6-8 introduces a halogen atom and an imidyl moiety to vicinal C-atoms of a carbon chain. With cyclic alkenes, the trans/cis-stereoselectivity depends on the nature of the imidyl unit, on the halogen atom, and on the alkene and varied between 58 : 42 and >95 : 5. Temperature dependend studies showed higher trans/cis-selectivities at elevated temperatures, which may be caused by different conformations of the adduct radicals 10-12, each of them exhibiting a different stereoselectivity.
