Literature DB >> 27428050

Palladium(II)-Catalyzed ortho-Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold.

Qiankun Li1, Brian J Knight1, Eric M Ferreira2.   

Abstract

A palladium(II)-catalyzed C-H arylation process of alcohols has been developed. The strategy utilizes a novel quinoline-based hemiacetal scaffold that can direct the selective C-H bond functionalization. This reaction provides a useful method to construct biaryl compounds of benzyl alcohols in good to excellent yields. The new molecular scaffold can be readily attached, removed, and recovered.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C coupling; C−H functionalization; arylation; palladium; quinoline acetal

Year:  2016        PMID： 27428050      PMCID： PMC5984652          DOI： 10.1002/chem.201602844

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  40 in total

1.  Iridium-catalyzed arene ortho-silylation by formal hydroxyl-directed C-H activation.

Authors:  Eric M Simmons; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

2.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

Review 3.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors:  Dino Alberico; Mark E Scott; Mark Lautens
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

Review 4.  Recent advances in aryl-aryl bond formation by direct arylation.

Authors:  Gerard P McGlacken; Lorraine M Bateman
Journal:  Chem Soc Rev       Date:  2009-05-22       Impact factor: 54.564

5.  Ruthenium(II)-catalyzed C-H bond activation and functionalization.

Authors:  Percia Beatrice Arockiam; Christian Bruneau; Pierre H Dixneuf
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

6.  Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

Authors:  Keary M Engle; Peter S Thuy-Boun; Michael Dang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

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

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

8.  Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle.

Authors:  Kun Guo; Xiaolan Chen; Mingyu Guan; Yingsheng Zhao
Journal:  Org Lett       Date:  2015-03-13       Impact factor: 6.005

9.  Transmetallation versus β-hydride elimination: the role of 1,4-benzoquinone in chelation-controlled arylation reactions with arylboronic acids.

Authors:  Christian Sköld; Jonatan Kleimark; Alejandro Trejos; Luke R Odell; Sten O Nilsson Lill; Per-Ola Norrby; Mats Larhed
Journal:  Chemistry       Date:  2012-02-28       Impact factor: 5.236

10.  Cross-coupling of remote meta-C-H bonds directed by a U-shaped template.

Authors:  Li Wan; Navid Dastbaravardeh; Gang Li; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-20       Impact factor: 15.419
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  2 in total

1.  Meta-Selective C-H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold.

Authors:  Qiankun Li; Eric M Ferreira
Journal:  Chemistry       Date:  2017-08-07       Impact factor: 5.236

2.  Empirical Guidelines for the Development of Remote Directing Templates through Quantitative and Experimental Analyses.

Authors:  Nelson Y S Lam; Zhoulong Fan; Kevin Wu; Han Seul Park; Su Yong Shim; Daniel A Strassfeld; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2022-02-02       Impact factor: 16.383
  2 in total

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