Sulfonylation of organometallic reagents with arenesulfonyl fluorides: a simple one-step synthesis of sulfones

…, EL Sullivan, KP Cusack, JM Funaro

Index: Frye, Leah L.; Sullivan, Eileen L.; Cusack, Kevin P.; Funaro, John M. Journal of Organic Chemistry, 1992 , vol. 57, # 2 p. 697 - 701

Full Text: HTML

Citation Number: 34

Abstract

Sulfonylation of organometallic reagents was accomplished with arenesulfonyl fluorides to provide a wide variety of alkylaryl-and diary1 sulfones. Organolithium and diorganocopper lithium reagents react smoothly with arenesulfonyl fluorides to give sulfones in high yields. Alkyl Grignard reagents often lead to mixtures of monosulfonylated and disulfonylated products. However, allylmagnesium chloride and phenylmagnesium chloride provide the ...

~31%

~92%

~82%

~77%

~85%

~99%

~20%

~94%

~10%

~89%

~12%

~60%

~92%

~87%

~73%

~13%

~12%

~17%

~95%

~69%

~17%

~69%

On the mechanism of the oxidation of tosylhydrazines by N-io...

[Yang, Ding-yah; Han, Oksoo; Liu, Hung-wen Journal of Organic Chemistry, 1989 , vol. 54, # 22 p. 5402 - 5406]

Iron (III) Chloride??Catalyzed Direct Sulfonylation of Alcoh...

[Reddy, M. Amarnath; Reddy, P. Surendra; Sreedhar Advanced Synthesis and Catalysis, 2010 , vol. 352, # 11-12 p. 1861 - 1869]

Organic reactions in ionic liquids: a new method for the syn...

[Hu, Yi; Chen, Zhen-Chu; Le, Zhang-Gao; Zheng, Qin-Guo Synthetic Communications, 2004 , vol. 34, # 21 p. 4031 - 4035]

Elimination–addition. Part XIII. Reactions of ω-bromoalkyl p...

[Knipe,A.C.; Stirling,C.J.M. Journal of the Chemical Society [Section] B: Physical Organic, 1967 , p. 808 - 814]