title: Preparation and purification of zinc sulfinate reagents for drug discovery.
abstract: The present protocol details the synthesis of zinc bis(alkanesulfinate)s that can be used as general reagents for the formation of radical species. The zinc sulfinates described herein are generated from the corresponding sulfonyl chlorides by treatment with zinc dust. The products may be used crude, or a simple purification procedure may be performed to minimize incorporation of water and zinc chloride. Although the synthesis of the zinc sulfinate salts can generally be completed within 3 h, workup can take up to 24 h and purification can take up to 3 h. Following the steps in this protocol would enable the user to generate a small toolkit of zinc sulfinate reagents over the course of 1 week.
authors: Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA.
authors: Fionn
authors: F
authors: O'Hara
authors: Ryan D
authors: RD
authors: Baxter
authors: Alexander G
authors: AG
authors: O'Brien
authors: Michael R
authors: MR
authors: Collins
authors: Janice A
authors: JA
authors: Dixon
authors: Yuta
authors: Y
authors: Fujiwara
authors: Yoshihiro
authors: Y
authors: Ishihara
authors: Phil S
authors: PS
authors: Baran
mesh_terms: D000476:Alkanesulfonates / Q000737:chemistry* / Q000302:isolation & purification*; D055808:Drug Discovery / Q000379:methods*; D008698:Mesylates / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D013441:Sulfinic Acids / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D000476:Alkanesulfonates; D008698:Mesylates; D013441:Sulfinic Acids; C044255:sulfonyl chloride; D015032:Zinc; C012077:trifluoromethanesulfonic acid
references: Acc Chem Res. 2012 Jun 19;45(6):826-39
references: 22017496
references: Org Lett. 2013 Jan 18;15(2):406-9
references: 23305217
references: Proc Natl Acad Sci U S A. 2011 Aug 30;108(35):14411-5
references: 21844378
references: Nature. 2012 Dec 6;492(7427):95-9
references: 23201691
references: J Am Chem Soc. 2012 Jan 25;134(3):1494-7
references: 22229949