The Journal of organic chemistry

Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents

SE Denmark, AJ Cresswell

Index: Denmark, Scott E.; Cresswell, Alexander J. Journal of Organic Chemistry, 2013 , vol. 78, # 24 p. 12593 - 12628

Full Text: HTML

Citation Number: 25

Abstract

The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition-metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate that enable the challenging oxidative addition to the C (sp3)–S bond. Through extensive optimization efforts, an Fe (acac) 3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl ...

~51%

~88%

~59%

~98%

~98%

Deoxygenative functionalization of hydroxy groups via xantha...

[Togo, Hideo; Matsubayashi, Sou; Yamazaki, Osamu; Yokoyama, Masataka Journal of Organic Chemistry, 2000 , vol. 65, # 9 p. 2816 - 2819]

Copper-catalyzed allylic alkylations of alkylzirconium inter...

[Venanzi, Luigi M.; Lehmann, Roman; Keil, Robert; Lipshutz, Bruce H. Tetrahedron Letters, 1992 , vol. 33, # 40 p. 5857 - 5860]