New reactivity of a reducing reagent generated from a copper(I) salt and a hydrosilane: Selective reduction of ketones and olefins conjugated with an aromatic group

Synlett

Volumn , Issue 4, 2000, Pages 479-482

  Ito, Hajime ^a   Yamanaka, Hiroshi ^b   Ishizuka, Tomoko ^b   Tateiwa, Jun Ichi ^b   Hosomi, Akira ^b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Alkenes; Copper; Ketones; Reductions; Silicon

Indexed keywords

ALKENE; AROMATIC COMPOUND; COPPER COMPLEX; KETONE; SILANE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0034087505     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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43. 2SiD, the incorporation of deuterium at the 2-and 3-positions of the reduced products was detected by NMR (Scheme 4). These results suggested that both of the deuterium atoms at 2-and 3-positions were provided by copper deuteride(I) or deuteriosilane. Organocopper(I) intermediates A derived from 4d presumably reacted with copper deuteride(I) or deuteriosilane to give deuterized products. However, an explanation including radical mechanism is also possible. For the reaction between organocopper(I) compounds and copper(I) hydride derivatives, see: ref. 5a.