MeOH or H2O as efficient additive to switch the reactivity of allylSmBr towards carbonyl compounds. Issue 13 (29th March 2017)

• Record Type: Journal Article
• Authors: Li, Jianyong; Niu, Qingsheng; Li, Shanchan; Sun, Yuehao; Zhou, Qian; Lv, Xin; Wang, Xiaoxia
• Is Part Of: Tetrahedron letters. Volume 58:Issue 13(2017)
• Page Start: 1250
• Page End: 1253
• Publication Date: 2017-03-29
• Subjects: Allylsamarium bromide -- MeOH -- H2O -- Pinacol coupling -- Diols; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.01.091
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr. MeOH switched allylSmBr from a nucleophile to good reductive coupling reagent. H2 O was useful additive to realize the coupling of aliphatic carbonyl compounds. AllylSmBr switched by greener additive is hopeful to find more applications. Abstract: A variety of carbonyl compounds were treated by allylSmBr (allylSmBr) with MeOH as the cosolvent to have further insights on the previously reported reductive coupling of aryl ketones mediated by Sm/alkyl halide/MeOH. The results demonstrate that the real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr, and MeOH has elegantly switched the reactivity of allylSmBr from being nucleophilic to being good reductive coupling reagent. Besides, H2 O was also found to be a useful additive to realize the pinacol coupling of aliphatic aldehydes and ketones promoted by allylSmBr.