Literature DB >> 24124892

Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Peter S Thuy-Boun1, Giorgio Villa, Devin Dang, Paul Richardson, Shun Su, Jin-Quan Yu.   

Abstract

A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.

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Year:  2013        PMID： 24124892      PMCID： PMC3879047          DOI： 10.1021/ja409014v

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


  56 in total

1.  Oxidation of alkyl trifluoroborates: an opportunity for tin-free radical chemistry.

Authors:  Geoffroy Sorin; Rocio Martinez Mallorquin; Yohan Contie; Alexandre Baralle; Max Malacria; Jean-Philippe Goddard; Louis Fensterbank
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

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.  Impact of natural products on developing new anti-cancer agents.

Authors:  Gordon M Cragg; Paul G Grothaus; David J Newman
Journal:  Chem Rev       Date:  2009-07       Impact factor: 60.622

4.  Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes.

Authors:  Guojun Deng; Liang Zhao; Chao-Jun Li
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  The First General Method for Stille Cross-Couplings of Aryl Chlorides.

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Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

Review 6.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

7.  Direct cross-coupling of C-H bonds with Grignard reagents through cobalt catalysis.

Authors:  Bin Li; Zhen-Hua Wu; Yi-Fan Gu; Chang-Liang Sun; Bai-Quan Wang; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-22       Impact factor: 15.336

8.  Cobalt-catalyzed ortho-alkylation of secondary benzamide with alkyl chloride through directed C-H bond activation.

Authors:  Quan Chen; Laurean Ilies; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2010-12-15       Impact factor: 15.419

9.  Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

Authors:  Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

10.  Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance.

Authors:  Yoshinori Aihara; Naoto Chatani
Journal:  J Am Chem Soc       Date:  2013-04-01       Impact factor: 15.419
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  20 in total

1.  Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors:  Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal:  Organic Synth       Date:  2015-03-12

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.  Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

Authors:  Alexander M Haydl; John F Hartwig
Journal:  Org Lett       Date:  2019-02-14       Impact factor: 6.005

4.  Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Authors:  Jian He; Ryosuke Takise; Haiyan Fu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-04-02       Impact factor: 15.419

Review 5.  A Simple and Versatile Amide Directing Group for C-H Functionalizations.

Authors:  Ru-Yi Zhu; Marcus E Farmer; Yan-Qiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-01       Impact factor: 15.336

6.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

7.  β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group.

Authors:  Tetsuya Toba; Yi Hu; Anh T Tran; Jin-Quan Yu
Journal:  Org Lett       Date:  2015-12-04       Impact factor: 6.005

8.  From Pd(OAc)2 to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Authors:  Qian Shao; Kevin Wu; Zhe Zhuang; Shaoqun Qian; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2020-03-31       Impact factor: 22.384

9.  Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with O2.

Authors:  Chase A Salazar; Kaylin N Flesch; Brandon E Haines; Philip S Zhou; Djamaladdin G Musaev; Shannon S Stahl
Journal:  Science       Date:  2020-11-19       Impact factor: 47.728

10.  Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F.

Authors:  Zhe Zhuang; Alastair N Herron; Shuang Liu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-01-04       Impact factor: 15.419
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