Dichloromethane as an unusual methylene equivalent. A new entry of highly nucleophilic and selective titanium-methylene complexes for ester methylenation

Tu-Hsin Yan; Ching-Ting Chien; Chia-Chung Tsai; Kuo-Wei Lin; Yen-Hsien Wu

doi:10.1021/ol047887e

Dichloromethane as an unusual methylene equivalent. A new entry of highly nucleophilic and selective titanium-methylene complexes for ester methylenation

Org Lett. 2004 Dec 23;6(26):4965-7. doi: 10.1021/ol047887e.

Authors

Tu-Hsin Yan¹, Ching-Ting Chien, Chia-Chung Tsai, Kuo-Wei Lin, Yen-Hsien Wu

Affiliation

¹ Department of Chemistry, National Chung-Hsing University, Taichung 400, Taiwan, Republic of China. thyan@mail.nchu.edu.tw

PMID: 15606111
DOI: 10.1021/ol047887e

Abstract

[reaction: see text] The successful application of CH2Cl2-Mg-TiCl4-system mediated methylenation of various esters such as tert-butyl ester and 2,5-cyclohexadiene-1-carboxylate highlights the extraordinary reactivity, selectivity, and the nonbasic nature of this new methylene-carbenoid, which serves as a practical reagent applicable to large-scale synthesis.