Literature DB >> 16928089

Synthesis of functionalized diarylmethanes via a copper-catalyzed cross-coupling of arylmagnesium reagents with benzylic phosphates.

Christiane C Kofink1, Paul Knochel.   

Abstract

A combination of copper chloride, triethyl phosphite, and tetrabutylammonium iodide is a very efficient catalytic system for the synthesis of polyfunctionalized diarylmethanes, using the cross-coupling reaction of arylmagnesium halides with benzylic phosphates. The antibiotic Trimethoprim has been prepared using this Cu(I)-catalyzed cross-coupling in 52% overall yield (four steps).

Entities:  

Year:  2006        PMID： 16928089     DOI： 10.1021/ol0616790

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


  10 in total

1.  "On water" sp3-sp2 cross-couplings between benzylic and alkenyl halides.

Authors:  Valeria Krasovskaya; Arkady Krasovskiy; Anish Bhattacharjya; Bruce H Lipshutz
Journal:  Chem Commun (Camb)       Date:  2011-04-12       Impact factor: 6.222

2.  Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates.

Authors:  Gary A Molander; Maxwell D Elia
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

3.  Feasible Synthesis of Antagonist of GPR40 by Constructing 2-Thiouracil Ring viaAcid Mediated Cyclization.

Authors:  Yongfeng Zhao; Yang Song; Xiulin Shen; Jiayu Liao
Journal:  Heterocycles       Date:  2011-05-01       Impact factor: 0.831

4.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

5.  Cross-couplings between benzylic and aryl halides "on water": synthesis of diarylmethanes.

Authors:  Christophe Duplais; Arkady Krasovskiy; Alina Wattenberg; Bruce H Lipshutz
Journal:  Chem Commun (Camb)       Date:  2009-12-09       Impact factor: 6.222

6.  Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation.

Authors:  Prantik Maity; Danielle M Shacklady-McAtee; Glenn P A Yap; Eric R Sirianni; Mary P Watson
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

7.  Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts.

Authors:  Sheng-Chun Sha; Sergei Tcyrulnikov; Minyan Li; Bowen Hu; Yue Fu; Marisa C Kozlowski; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2018-09-19       Impact factor: 15.419

8.  Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

Authors:  Jennie Liao; Weiye Guan; Brian P Boscoe; Joseph W Tucker; John W Tomlin; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2018-05-10       Impact factor: 6.005

9.  Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides.

Authors:  Laura K G Ackerman; Lukiana L Anka-Lufford; Marina Naodovic; Daniel J Weix
Journal:  Chem Sci       Date:  2014-11-10       Impact factor: 9.825

10.  Synthesis, Kinetic and Conformational Studies of 2-Substituted-5-(β-d-glucopyranosyl)-pyrimidin-4-ones as Potential Inhibitors of Glycogen Phosphorylase.

Authors:  Konstantinos F Mavreas; Dionysios D Neofytos; Evangelia D Chrysina; Alessandro Venturini; Thanasis Gimisis
Journal:  Molecules       Date:  2020-11-22       Impact factor: 4.411
  10 in total

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