Literature DB >> 23597105

Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3.

Sharon R Neufeldt1, Cydney K Seigerman, Melanie S Sanford.   

Abstract

A Pd-catalyzed method for ligand-directed C-H alkylation with organoboron reagents is described. The combination of potassium organotrifluoroborates, MnF3, and a Pd(II) catalyst effects pyridine and amide-directed C-H alkylation. These reactions proceed under mild conditions (25-40 °C in weakly acidic media), are effective for installing methyl and 1° alkyl groups, and do not require promoters such as benzoquinone.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23597105      PMCID： PMC3670967          DOI： 10.1021/ol400888r

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


  36 in total

1.  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 2.  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 3.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate.

Authors:  Wing-Yiu Yu; Wing Nga Sit; Kin-Man Lai; Zhongyuan Zhou; Albert S C Chan
Journal:  J Am Chem Soc       Date:  2008-02-26       Impact factor: 15.419

Review 5.  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

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

Review 7.  High-valent organometallic copper and palladium in catalysis.

Authors:  Amanda J Hickman; Melanie S Sanford
Journal:  Nature       Date:  2012-04-11       Impact factor: 49.962

8.  Palladium(II)-catalyzed ortho alkylation of benzoic acids with alkyl halides.

Authors:  Yang-Hui Zhang; Bing-Feng Shi; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

Authors:  Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 10.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
View more
  10 in total

1.  Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a MnIII Oxidant under Mild Conditions.

Authors:  Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

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

Authors:  Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-08       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.  Iridium-catalysed arylation of C-H bonds enabled by oxidatively induced reductive elimination.

Authors:  Kwangmin Shin; Yoonsu Park; Mu-Hyun Baik; Sukbok Chang
Journal:  Nat Chem       Date:  2017-12-11       Impact factor: 24.427

5.  Electrochemical Fluorination of Vinyl Boronates through Donor-Stabilized Vinyl Carbocation Intermediates.

Authors:  Benjamin Wigman; Woojin Lee; Wenjing Wei; Kendall N Houk; Hosea M Nelson
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-03       Impact factor: 15.336

6.  Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors:  Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2013-09-19       Impact factor: 4.354

7.  Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Org Lett       Date:  2013-06-04       Impact factor: 6.005

8.  Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated via C(sp3)-H activation.

Authors:  Zhuo Wu; Hang Jiang; Yanghui Zhang
Journal:  Chem Sci       Date:  2021-05-19       Impact factor: 9.825

9.  Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study.

Authors:  A Gray; A Tsybizova; J Roithova
Journal:  Chem Sci       Date:  2015-07-01       Impact factor: 9.825

10.  Selective C-H Olefination of Indolines (C5) and Tetrahydroquinolines (C6) by Pd/S,O-Ligand Catalysis.

Authors:  Wen-Liang Jia; Nick Westerveld; Kit Ming Wong; Thomas Morsch; Matthijs Hakkennes; Kananat Naksomboon; M Ángeles Fernández-Ibáñez
Journal:  Org Lett       Date:  2019-11-11       Impact factor: 6.005
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.