Ether derivatization via two-step protocol comprised of photochemical ethereal C–H bond chlorination and nucleophilic substitution. Issue 14 (1st April 2015)

• Record Type: Journal Article
• Authors: Kamijo, Shin; Tao, Keisuke; Takao, Go; Murooka, Hironori; Murafuji, Toshihiro
• Is Part Of: Tetrahedron letters. Volume 56:Issue 14(2015)
• Page Start: 1904
• Page End: 1907
• Publication Date: 2015-04-01
• Subjects: Carbon tetrachloride -- Chlorination -- Ether -- Sulfamoyl chloride -- Photoreaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.02.102
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A two-step protocol has been developed for ether derivatization introducing oxygen-, sulfur-, and carbon-functionalities. The present protocol comprises photochemical chlorination of ethereal C(sp 3 )–H bond for preparation of chlorinated ethers as common synthetic intermediates, and nucleophilic substitution of the installed chlorine moiety for construction of various ether derivatives. These two reactions can be conducted sequentially in a single flask, thus the newly developed method offers a one-pot and unified procedure for ether derivatization with attachment of various functionalities at the α-position.