Making more efficient lithium carbenoid reagents for cyclopropanation by hetero-aggregation: A DFT prediction on a new factor to control the SN2-Type organometallic reaction

Publication date: Available online 14 March 2018 Source:Journal of Organometallic Chemistry Author(s): Youxiang Shao, Xiao Huang, Cunyuan Zhao, Zhuofeng Ke Lithium carbenoids are important reagents in organic synthesis. Systemic DFT calculations have been carriered out to reveal the influence of hetero-aggregation states on the reactivity of lithium carbenoid reagents. The resutls indicate that the cyclopropanation reaction could be accelerated dramatically by hetero-aggregated lithium carbenoids with a halogen or oxygen as an α-heteroatom. The origin of the enhancement could attribute to the novel structural character of the hetero-aggregated lithium carbenoids. These intriguing finding predicts that it is pratical to control a wide range of SN2-type organometallic reactions by using aggregated lithium carbenoids with other economical and convenient compounds. Graphical abstract

Source: Journal of Organometallic Chemistry - March 14, 2018 Category: Chemistry Source Type: research