Literature DB >> 20812668

Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagents.

Jonathan T Reeves1, Daniel R Fandrick, Zhulin Tan, Jinhua J Song, Heewon Lee, Nathan K Yee, Chris H Senanayake.   

Abstract

Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functionality is tolerated. Competition experiments established the reactivity of PhNMe(3)OTf relative to PhCl, PhBr, PhI, and PhOTf.

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Year:  2010        PMID： 20812668     DOI： 10.1021/ol1018739

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


  8 in total

1.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

2.  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

3.  Regio- and stereospecific rhodium-catalyzed allylic alkylation with an acyl anion equivalent: an approach to acyclic α-ternary β,γ-unsaturated aryl ketones.

Authors:  Ben W H Turnbull; Jungha Chae; Samuel Oliver; P Andrew Evans
Journal:  Chem Sci       Date:  2017-03-31       Impact factor: 9.825

4.  Cross-coupling polycondensation via C-O or C-N bond cleavage.

Authors:  Ze-Kun Yang; Ning-Xin Xu; Ryo Takita; Atsuya Muranaka; Chao Wang; Masanobu Uchiyama
Journal:  Nat Commun       Date:  2018-04-23       Impact factor: 14.919

5.  Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes.

Authors:  Alexander W Rand; John Montgomery
Journal:  Chem Sci       Date:  2019-04-26       Impact factor: 9.825

6.  Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel-Crafts reaction.

Authors:  Yafang Dong; Masahiko Sakai; Kazuto Fuji; Kohei Sekine; Yoichiro Kuninobu
Journal:  Beilstein J Org Chem       Date:  2020-03-17       Impact factor: 2.883

7.  Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene-palladium(ii) precatalyst.

Authors:  Tao Wang; Jiarui Guo; Xiaojuan Wang; Han Guo; Dingli Jia; Hengjin Wang; Lantao Liu
Journal:  RSC Adv       Date:  2019-02-15       Impact factor: 3.361

8.  Stille coupling via C-N bond cleavage.

Authors:  Dong-Yu Wang; Masatoshi Kawahata; Ze-Kun Yang; Kazunori Miyamoto; Shinsuke Komagawa; Kentaro Yamaguchi; Chao Wang; Masanobu Uchiyama
Journal:  Nat Commun       Date:  2016-09-30       Impact factor: 14.919
  8 in total

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