A New Route to E‐Stilbenes through the Transition‐Metal‐Free KOtBu/DMF‐Promoted Direct Coupling of Alcohols with Phenyl Acetonitriles. Issue 26 (9th July 2022)

• Record Type: Journal Article
• Authors: Liu, Xiaoping; Sotiropoulos, Jean‐Marc; Taillefer, Marc
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 26(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-09
• Subjects: Alkene synthesis -- Alcohol activation -- Transition metal free -- Mechanistic study -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200631
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An alternative route to synthesise alkenes, based only on the KO t Bu/DMF promoted activation and direct coupling of alcohols with phenyl acetonitriles, is reported. Various E ‐stilbenes have thus been obtained directly from alcohols that are sustainable sources of carbon, which to our knowledge, is unprecedented in the absence of transition metal based catalysts. A variation allowing, through a Csp3 −Csp3 bond formation, the selective synthesis of N ‐Heteroarenes is also described. A mechanism for the olefination pathway proceeding via an original activation of alcohols under alkyl formates is provided. Abstract : A new route to E ‐Stilbenes, based on the transition metal free, KO t Bu/DMF promoted activation and direct coupling of alcohols with phenyl acetonitriles, is reported. A variation allowing the selective synthesis of N‐Heteroarenes and a mechanism proceeding via the activation of alcohols under alkyl formate intermediates are also reported.