Literature DB >> 16956180

Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

Zigang Li1, Junliang Zhang, Chad Brouwer, Cai-Guang Yang, Nicholas W Reich, Chuan He.   

Abstract

Intermolecular addition of phenols, carboxylic acids, and protected amines to inert olefins can be catalyzed by low concentrations (1-5%) of triflic acid. Functional groups, such as the methoxyl substitution on aromatics, could be tolerated if the concentration of triflic acid and the reaction temperature are controlled appropriately. This reaction provides one of the simplest olefin addition methods and is an alternative to metal-catalyzed reactions.

Entities:  

Year:  2006        PMID: 16956180     DOI: 10.1021/ol0610035

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  37 in total

1.  Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.

Authors:  Tejas P Pathak; Jaroslaw G Osiak; Rachel M Vaden; Bryan E Welm; Matthew S Sigman
Journal:  Tetrahedron       Date:  2012-07-01       Impact factor: 2.457

2.  Base- and ligand-free room-temperature synthesis of N-fused heteroaromatic compounds via the transition metal-catalyzed cycloisomerization protocol.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-07-17       Impact factor: 6.005

3.  Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors:  Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 4.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

5.  Organic chemistry: Metals are not the only catalysts.

Authors:  Matthew Gaunt
Journal:  Nature       Date:  2011-02-10       Impact factor: 49.962

6.  Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Authors:  Mary M Rozenman; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-11-10       Impact factor: 15.419

7.  Coupling Pd-Catalyzed Alcohol Oxidation to Olefin Functionalization: Hydrohalogenation/Hydroalkoxylation of Styrenes.

Authors:  Susanne M Podhajsky; Matthew S Sigman
Journal:  Organometallics       Date:  2007-11-05       Impact factor: 3.876

8.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

9.  Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes.

Authors:  Xiaoming Zeng; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

10.  Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

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