Literature DB >> 19283811

Asymmetric Suzuki-Miyaura coupling in water with a chiral palladium catalyst supported on an amphiphilic resin.

Yasuhiro Uozumi1, Yutaka Matsuura, Takayasu Arakawa, Yoichi M A Yamada.   

Abstract

You oughta use water: Broad functional-group (FG) tolerance was observed for the title coupling of aryl halides (X = Cl, Br, I) and aryl boronic acids to give biaryl compounds with up to 94% ee. The chiral imidazoindole phosphine-palladium catalyst supported on an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin could be recycled readily.

Entities:  

Year:  2009        PMID： 19283811     DOI： 10.1002/anie.200900469

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki-Miyaura reaction: substrate scope and quantum mechanical investigations.

Authors:  Xiaoqiang Shen; Gavin O Jones; Donald A Watson; Brijesh Bhayana; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

3.  Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates.

Authors:  Scott E Denmark; Wen-Tau T Chang; K N Houk; Peng Liu
Journal:  J Org Chem       Date:  2014-12-10       Impact factor: 4.354

4.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

5.  Organocatalytic atroposelective synthesis of axially chiral styrenes.

Authors:  Sheng-Cai Zheng; San Wu; Qinghai Zhou; Lung Wa Chung; Liu Ye; Bin Tan
Journal:  Nat Commun       Date:  2017-05-03       Impact factor: 14.919

6.  Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

Authors:  Changgui Zhao; Donghui Guo; Kristin Munkerup; Kuo-Wei Huang; Fangyi Li; Jian Wang
Journal:  Nat Commun       Date:  2018-02-09       Impact factor: 14.919

Review 7.  Recent applications of polymer supported organometallic catalysts in organic synthesis.

Authors:  Nina Kann
Journal:  Molecules       Date:  2010-09-07       Impact factor: 4.411

8.  Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts.

Authors:  Shoma Ikeda; Ryohei Takeda; Takaya Fujie; Naoto Ariki; Yuuya Nagata; Michinori Suginome
Journal:  Chem Sci       Date:  2021-05-26       Impact factor: 9.825

9.  P(O)R2-directed Pd-catalyzed C-H functionalization of biaryl derivatives to synthesize chiral phosphorous ligands.

Authors:  Rong-Bin Hu; Hong-Li Wang; Hong-Yu Zhang; Heng Zhang; Yan-Na Ma; Shang-Dong Yang
Journal:  Beilstein J Org Chem       Date:  2014-09-02       Impact factor: 2.883

10.  An enantioselective artificial Suzukiase based on the biotin-streptavidin technology.

Authors:  Anamitra Chatterjee; Hendrik Mallin; Juliane Klehr; Jaicy Vallapurackal; Aaron D Finke; Laura Vera; May Marsh; Thomas R Ward
Journal:  Chem Sci       Date:  2015-10-19       Impact factor: 9.825
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