Literature DB >> 24325399

Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Sunggi Lee1, Hyelee Lee, Kian L Tan.   

Abstract

A nitrile-based template that enables meta-selective C-H bond functionalization was developed. The template is applicable to a range of substituted arenes and tolerates a variety of functional groups. The directing group uses a silicon atom for attachment, allowing for a facile introduction/deprotection strategy increasing the synthetic practicality of this template.

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Year:  2013        PMID： 24325399      PMCID： PMC3929498          DOI： 10.1021/ja4107034

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


  56 in total

Review 1.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

2.  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

3.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

Review 4.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

5.  Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent.

Authors:  Tatsuo Ishiyama; Yusuke Nobuta; John F Hartwig; Norio Miyaura
Journal:  Chem Commun (Camb)       Date:  2003-12-07       Impact factor: 6.222

6.  Pd-catalyzed modifiable silanol-directed aromatic C-H oxygenation.

Authors:  Chunhui Huang; Nugzar Ghavtadze; Benhur Godoi; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2012-07-02       Impact factor: 5.236

7.  Pd(II)-catalyzed ortho- or meta-C-H olefination of phenol derivatives.

Authors:  Hui-Xiong Dai; Gang Li; Xing-Guo Zhang; Antonia F Stepan; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-05-08       Impact factor: 15.419

Review 8.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

9.  Direct coupling of benzene with olefin catalyzed by Pd(OAc)(2) combined with heteropolyoxometalate under dioxygen.

Authors:  Takahiro Yokota; Masayuki Tani; Satoshi Sakaguchi; Yasutaka Ishii
Journal:  J Am Chem Soc       Date:  2003-02-12       Impact factor: 15.419

10.  TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines.

Authors:  Chunhui Huang; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419
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  25 in total

1.  Silicon-Tethered Strategies for C-H Functionalization Reactions.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Acc Chem Res       Date:  2017-08-03       Impact factor: 22.384

2.  Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene.

Authors:  Peng-Xiang Shen; Xiao-Chen Wang; Peng Wang; Ru-Yi Zhu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-09-03       Impact factor: 15.419

3.  Remote site-selective C-H activation directed by a catalytic bifunctional template.

Authors:  Zhipeng Zhang; Keita Tanaka; Jin-Quan Yu
Journal:  Nature       Date:  2017-03-08       Impact factor: 49.962

4.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

Review 5.  Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach.

Authors:  Guangrong Meng; Nelson Y S Lam; Erika L Lucas; Tyler G Saint-Denis; Pritha Verma; Nikita Chekshin; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-06-05       Impact factor: 15.419

6.  Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay.

Authors:  Kohki M Nakafuku; Raymond K Twumasi; Avassaya Vanitcha; Ethan A Wappes; Kayambu Namitharan; Mathieu Bekkaye; David A Nagib
Journal:  J Org Chem       Date:  2019-09-12       Impact factor: 4.354

7.  General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation.

Authors:  Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-19       Impact factor: 15.336

8.  Ligand-enabled meta-C-H activation using a transient mediator.

Authors:  Xiao-Chen Wang; Wei Gong; Li-Zhen Fang; Ru-Yi Zhu; Suhua Li; Keary M Engle; Jin-Quan Yu
Journal:  Nature       Date:  2015-03-09       Impact factor: 49.962

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

Authors:  Qiankun Li; Brian J Knight; Eric M Ferreira
Journal:  Chemistry       Date:  2016-08-05       Impact factor: 5.236

10.  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
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