28046-85-7Relevant academic research and scientific papers
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.
Stereoretentive halogenations and azidations with titanium(IV) enabled by chelating leaving groups
Lepore, Salvatore D.,Mondal, Deboprosad,Song, Ye Li,Bhunia, Anjan K.
supporting information; body text, p. 7511 - 7514 (2009/03/12)
Titaniumdoes it again! With the help of nucleophile-assisting leaving groups (NALGs), alkyl bromides, iodides, and, for the first time, azides are obtained from sulfonates withcomplete retention of configuration. Critical to the design of these new titanium(IV) reactions has been the use of NALGs which are thought to chelate the Lewis acid reagent in the transition state promoting an SNi-type mechanism. (Chemical Equation Presented)
A CONVENIENT STEREOSPECIFIC ALKYLATION OF PHENYLACETYLENE BY ELECTROCHEMICAL REACTION OF ORGANOBORANES
Takahashi, Yuzuru,Tokuda, Masao,Itoh, Mitsuomi,Suzuki, Akira
, p. 461 - 464 (2007/10/02)
The electrochemical reaction of phenylacetylene with trialkylboranes in a tetrahydrofuran solution containing tetraalkylammonium halide gives the corresponding alkynes via a retention of configuration with respect to the boron-carbon bonds.The reaction mechanism is also discussed.
