Capture of In Situ Generated Diazo Compounds or Copper Carbenoids by Triphenylphosphine: Selective Synthesis of trans‐ Alkenes and Unsymmetric Azines via Reaction of Aldehydes with Ketone‐Derived N‐Tosylhydrazones. Issue 11 (9th August 2013)

• Record Type: Journal Article
• Authors: Sha, Qiang; Ling, Yifei; Wang, Wenyong; Wei, Yunyang
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 11/12(2013)
• Page Start: 2145
• Page End: 2150
• Publication Date: 2013-08-09
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300302
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Copper(II) acetylacetonate‐catalyzed Wittig olefination reactions of aldehydes with ketone‐derived <italic>N</italic>‐tosylhydrazones are reported. A series of tosylhydrazones was investigated and our results showed that the carbon number of the alkyl chain influences the <italic>E</italic>‐selecivity of the alkenes greatly. Alkenes could be obtained in moderate yields and excellent <italic>E</italic>‐selectivity when the carbon numbers were up to two. Under metal‐free conditions, triphenylphosphine was able to capture the <italic>in situ</italic> generated diazo compounds and the corresponding unsymmetrical azines were formed in good yields.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg36h126sq" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>