Literature DB >> 23909907

Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

M Alexander Düfert1, Kelvin L Billingsley, Stephen L Buchwald.   

Abstract

The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in good to excellent yields. Additionally, the mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.

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Year:  2013        PMID： 23909907      PMCID： PMC3807799          DOI： 10.1021/ja4064469

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


  48 in total

1.  One-pot two-step microwave-assisted reaction in constructing 4,5-disubstituted pyrazolopyrimidines.

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Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

Review 2.  Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

Authors:  Mélanie Platon; Régine Amardeil; Laurent Djakovitch; Jean-Cyrille Hierso
Journal:  Chem Soc Rev       Date:  2012-03-26       Impact factor: 54.564

3.  Ligand-free Pd/C-catalyzed Suzuki-Miyaura coupling reaction for the synthesis of heterobiaryl derivatives.

Authors:  Yoshiaki Kitamura; Satoko Sako; Takahiro Udzu; Azusa Tsutsui; Tomohiro Maegawa; Yasunari Monguchi; Hironao Sajiki
Journal:  Chem Commun (Camb)       Date:  2007-10-02       Impact factor: 6.222

4.  Design and synthesis of 6-anilinoindazoles as selective inhibitors of c-Jun N-terminal kinase-3.

Authors:  Britt-Marie Swahn; Fernando Huerta; Elisabet Kallin; Jonas Malmström; Tatjana Weigelt; Jenny Viklund; Patrick Womack; Yafeng Xue; Liselotte Ohberg
Journal:  Bioorg Med Chem Lett       Date:  2005-11-15       Impact factor: 2.823

5.  A new biarylphosphine ligand for the Pd-catalyzed synthesis of diaryl ethers under mild conditions.

Authors:  Luca Salvi; Nicole R Davis; Siraj Z Ali; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-12-19       Impact factor: 6.005

6.  Efficient Pd-catalyzed amination reactions for heterocycle functionalization.

Authors:  Jaclyn L Henderson; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

7.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

8.  Alkylboranes in the Suzuki-Miyaura Coupling: Stereochemical and Mechanistic Studies.

Authors:  Karl Matos; John A. Soderquist
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

9.  Arylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partner role swapping and heterocycle protection.

Authors:  Monica Prieto; Esther Zurita; Esmeralda Rosa; Lourdes Muñoz; Paul Lloyd-Williams; Ernest Giralt
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

10.  Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents.

Authors:  Paul Knochel; Matthias A Schade; Sebastian Bernhardt; Georg Manolikakes; Albrecht Metzger; Fabian M Piller; Christoph J Rohbogner; Marc Mosrin
Journal:  Beilstein J Org Chem       Date:  2011-09-13       Impact factor: 2.883
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  25 in total

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Authors:  Landon J Durak; James T Payne; Jared C Lewis
Journal:  ACS Catal       Date:  2016-01-25       Impact factor: 13.084

2.  Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

Authors:  Kyle Clagg; Haiyun Hou; Adam B Weinstein; David Russell; Shannon S Stahl; Stefan G Koenig
Journal:  Org Lett       Date:  2016-07-12       Impact factor: 6.005

3.  HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature.

Authors:  Sachin Handa; Martin P Andersson; Fabrice Gallou; John Reilly; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-29       Impact factor: 15.336

4.  Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Heterocycles.

Authors:  Hasnain A Malik; Buck L H Taylor; John R Kerrigan; Jonathan E Grob; K N Houk; J Du Bois; Lawrence G Hamann; Andrew W Patterson
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

5.  Well-defined nickel and palladium precatalysts for cross-coupling.

Authors:  Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal:  Nat Rev Chem       Date:  2017-03-01       Impact factor: 34.035

6.  Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.

Authors:  Xi-Jie Dai; Oliver D Engl; Thierry León; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

7.  Off-Cycle Processes in Pd-Catalyzed Cross-Coupling of Carboranes.

Authors:  Rafal M Dziedzic; Jonathan C Axtell; Arnold L Rheingold; Alexander M Spokoyny
Journal:  Org Process Res Dev       Date:  2019-08-05       Impact factor: 3.317

8.  Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate.

Authors:  Vincent M Kassel; Christopher M Hanneman; Connor P Delaney; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

9.  Efficient microwave-assisted Suzuki-Miyaura cross-coupling reaction of 3-bromo pyrazolo[1,5-a]pyrimidin-5(4H)-one: towards a new access to 3,5-diarylated 7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine derivatives.

Authors:  Badr Jismy; Gérald Guillaumet; Mohamed Akssira; Abdellatif Tikad; Mohamed Abarbri
Journal:  RSC Adv       Date:  2021-01-04       Impact factor: 4.036

10.  Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities.

Authors:  John T Gupton; Scott Yeudall; Nakul Telang; Megan Hoerrner; Ellis Huff; Evan Crawford; Katie Lounsbury; Michael Kimmel; William Curry; Andrew Harrison; Wen Juekun; Alex Shimozono; Joe Ortolani; Kristin Lescalleet; Jon Patteson; Veronica Moore-Stoll; Cristina C Rohena; Susan L Mooberry; Ahmad J Obaidullah; Glen E Kellogg; James A Sikorski
Journal:  Bioorg Med Chem       Date:  2017-04-11       Impact factor: 3.641
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