Literature DB >> 19663513

Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

Takashi Nishikata1, Bruce H Lipshutz.   

Abstract

The first examples of Suzuki-Miyaura couplings of allylic ethers are reported. These can be done not only under very mild room-temperature conditions but also in water as the only medium. The process is made possible by micellar catalysis using the designer surfactant PTS.

Entities:  

Year:  2009        PMID： 19663513      PMCID： PMC3359317          DOI： 10.1021/ja905082c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids.

Authors:  George W Kabalka; Gang Dong; Bollu Venkataiah
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005

2.  Heck couplings at room temperature in nanometer aqueous micelles.

Authors:  Bruce H Lipshutz; Benjamin R Taft
Journal:  Org Lett       Date:  2008-03-12       Impact factor: 6.005

3.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors:  Sean A Reed; M Christina White
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

4.  Fast and highly regioselective allylation of indole and pyrrole compounds by allyl alcohols using Ru-sulfonate catalysts.

Authors:  Alexey B Zaitsev; Stefan Gruber; Pascal A Plüss; Paul S Pregosin; Luis F Veiros; Michael Wörle
Journal:  J Am Chem Soc       Date:  2008-08-06       Impact factor: 15.419

5.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

6.  Cross-Coupling of Aryl Halides and Allyl Acetates with Arylboron Reagents in Water Using an Amphiphilic Resin-Supported Palladium Catalyst.

Authors:  Yasuhiro Uozumi; Hiroshi Danjo; Tamio Hayashi
Journal:  J Org Chem       Date:  1999-04-30       Impact factor: 4.354

7.  Palladium pincer-complex catalyzed allylation of tosylimines by potassium trifluoro(allyl)borates.

Authors:  Niclas Solin; Olov A Wallner; Kálmán J Szabó
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

8.  Facile and selective deallylation of allyl ethers using diphosphinidenecyclobutene-coordinated palladium catalysts.

Authors:  Hiromi Murakami; Tatsuya Minami; Fumiyuki Ozawa
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

9.  Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

Authors:  Mamoru Tobisu; Toshiaki Shimasaki; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Preparation and coordination properties including catalytic activities of a bulky 2-methyl-3-thioxo-1,3-diphosphapropene.

Authors:  Hongze Liang; Shigekazu Ito; Masaaki Yoshifuji
Journal:  Org Lett       Date:  2004-02-05       Impact factor: 6.005
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  16 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  Nickel-catalyzed allylic substitution of simple alkenes.

Authors:  Ryosuke Matsubara; Timothy F Jamison
Journal:  Chem Asian J       Date:  2011-03-08

3.  Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.

Authors:  Thomas J A Graham; Abigail G Doyle
Journal:  Org Lett       Date:  2012-03-02       Impact factor: 6.005

4.  Nickel-catalyzed allylic substitution of simple alkenes.

Authors:  Ryosuke Matsubara; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

5.  Cationic Pd(II)-catalyzed Fujiwara-Moritani reactions at room temperature in water.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

6.  Room temperature C-H activation and cross-coupling of aryl ureas in water.

Authors:  Takashi Nishikata; Alexander R Abela; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

7.  Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

Authors:  Kevin T Sylvester; Kevin Wu; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419

8.  Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

Authors:  Stefan R K Minkler; Nicholas A Isley; Daniel J Lippincott; Norbert Krause; Bruce H Lipshutz
Journal:  Org Lett       Date:  2014-01-16       Impact factor: 6.005

9.  Amination of allylic alcohols in water at room temperature.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  Aminations of allylic phenyl ethers via micellar catalysis at room temperature in water.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  Chem Commun (Camb)       Date:  2009-09-08       Impact factor: 6.222
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