1244029-91-1Relevant academic research and scientific papers
Au–Ag Bimetallic Catalysis: 3-Alkynyl Benzofurans from Phenols via Tandem C?H Alkynylation/Oxy-Alkynylation
Hu, Long,Dietl, Martin C.,Han, Chunyu,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 10637 - 10642 (2021)
The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C?H alkynylation of phenols and oxy-alkynylation of the newly introduced triple bond by using a unique redox property and the carbophilic π acidity of gold. Mechanistic studies support the participation of a bimetallic gold–silver species. The one-pot protocol offers a direct, simple, and regio-specific approach to 3-alkynyl benzofurans from readily available phenols. A broad range of substrates, including heterocycles, is transferred with excellent functional group tolerance. Thus, this methodology can be used for the late-stage incorporation of benzofurans.
Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans
Xia, Zhonghua,Khaled, Omar,Mouriès-Mansuy, Virginie,Ollivier, Cyril,Fensterbank, Louis
, p. 7182 - 7190 (2016/08/30)
A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient app
Domino rhodium(I)-catalysed reactions for the efficient synthesis of substituted benzofurans and indoles
Boyer, Alistair,Isono, Naohiro,Lackner, Sebastian,Lautens, Mark
supporting information; experimental part, p. 6468 - 6482 (2010/10/03)
Rhodium(I) catalysts promote the transformation of o-alkynyl phenols and anilines to the corresponding benzo[b]furans and indoles. The reaction is postulated to proceed via a transient 3-rhodium heterocycle intermediate, which can be trapped with suitable electrophiles to give poly-substituted heterocycles. In the case of mono-substituted electron-withdrawn electrophiles, excellent yield and selectivity for conjugate addition versus Heck-Mizoroki reaction can be achieved. In the case of 2-alkynyl pyridine electrophiles, novel 2-(benzofuran-3-yl)vinylpyridines are formed.
