Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes. Issue 2 (8th December 2016)

• Record Type: Journal Article
• Authors: Bucher, Janina; Wurm, Thomas; Taschinski, Svenja; Sachs, Eleni; Ascough, David; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 2(2017)
• Page Start: 225
• Page End: 233
• Publication Date: 2016-12-08
• Subjects: diynes -- dual activation -- fluorenes -- gold catalysis -- gold vinylidenes; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600987
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 1, 5‐ Diyne systems bearing one terminal and one benzyl‐ or allyl‐substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold‐catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C( sp 2 )–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9 H ‐fluorene and 11 H ‐benzo[ b ]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10 H ‐benzo[ b ]fluorene derivatives are obtained in high yield. Abstract :