Literature DB >> 20860403

Efficient Pd-catalyzed amination reactions for heterocycle functionalization.

Jaclyn L Henderson1, Stephen L Buchwald.   

Abstract

The Pd-catalyzed amination of unprotected benzo-fused heterocycles is reported, which allows for greater flexibility and efficiency in the modification of this important class of molecules. The generality of these simple and efficient procedures is demonstrated through the synthesis of a wide variety of structural types.

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Year:  2010        PMID： 20860403      PMCID： PMC3164313          DOI： 10.1021/ol101929v

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


  19 in total

1.  Efficient pd-catalyzed amination of heteroaryl halides.

Authors:  Mark D Charles; Phillip Schultz; Stephen L Buchwald
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  Discovery of a (1H-benzoimidazol-2-yl)-1H-pyridin-2-one (BMS-536924) inhibitor of insulin-like growth factor I receptor kinase with in vivo antitumor activity.

Authors:  Mark Wittman; Joan Carboni; Ricardo Attar; Balu Balasubramanian; Praveen Balimane; Patrick Brassil; Francis Beaulieu; Chiehying Chang; Wendy Clarke; Janet Dell; Jeffrey Eummer; David Frennesson; Marco Gottardis; Ann Greer; Steven Hansel; Warren Hurlburt; Bruce Jacobson; Subramaniam Krishnananthan; Francis Y Lee; Aixin Li; Tai-An Lin; Peiying Liu; Carl Ouellet; Xiaopeng Sang; Mark G Saulnier; Karen Stoffan; Yax Sun; Upender Velaparthi; Henry Wong; Zheng Yang; Kurt Zimmermann; Mary Zoeckler; Dolatrai Vyas
Journal:  J Med Chem       Date:  2005-09-08       Impact factor: 7.446

3.  Investigation of various N-heterocyclic substituted piperazine versions of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol: effect on affinity and selectivity for dopamine D3 receptor.

Authors:  Dennis A Brown; Manoj Mishra; Suhong Zhang; Swati Biswas; Ingrid Parrington; Tamara Antonio; Maarten E A Reith; Aloke K Dutta
Journal:  Bioorg Med Chem       Date:  2009-04-19       Impact factor: 3.641

4.  Design and synthesis of rho kinase inhibitors (III).

Authors:  Masayuki Iwakubo; Atsuya Takami; Yuji Okada; Takehisa Kawata; Yoshimichi Tagami; Motoko Sato; Terumi Sugiyama; Kayoko Fukushima; Shinichiro Taya; Mutsuki Amano; Kozo Kaibuchi; Hiroshi Iijima
Journal:  Bioorg Med Chem       Date:  2006-10-18       Impact factor: 3.641

Review 5.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Indazoles: regioselective protection and subsequent amine coupling reactions.

Authors:  David J Slade; Nicholas F Pelz; Wanda Bodnar; John W Lampe; Paul S Watson
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

7.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  An efficient process for pd-catalyzed C-N cross-coupling reactions of aryl iodides: insight into controlling factors.

Authors:  Brett P Fors; Nicole R Davis; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

9.  Design, structure-activity relationships and in vivo characterization of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-ones: a novel class of receptor tyrosine kinase inhibitors.

Authors:  Paul A Renhowe; Sabina Pecchi; Cynthia M Shafer; Timothy D Machajewski; Elisa M Jazan; Clarke Taylor; William Antonios-McCrea; Christopher M McBride; Kelly Frazier; Marion Wiesmann; Gena R Lapointe; Paul H Feucht; Robert L Warne; Carla C Heise; Daniel Menezes; Kimberly Aardalen; Helen Ye; Molly He; Vincent Le; Jayesh Vora; Johanna M Jansen; Mary Ellen Wernette-Hammond; Alex L Harris
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446

10.  Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes.

Authors:  John F Hartwig
Journal:  Inorg Chem       Date:  2007-03-19       Impact factor: 5.165
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  12 in total

1.  Palladium-Catalyzed Arylation of Fluoroalkylamines.

Authors:  Andrew T Brusoe; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

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.  P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

Authors:  Gen Li; Ziyang Qin; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

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

Authors:  M Alexander Düfert; Kelvin L Billingsley; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-08-16       Impact factor: 15.419

5.  Total synthesis guided structure elucidation of (+)-psychotetramine.

Authors:  Klement Foo; Timothy Newhouse; Ikue Mori; Hiromitsu Takayama; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-17       Impact factor: 15.336

6.  Palladium-catalyzed C,N-cross coupling reactions of 3-halo-2-aminopyridines.

Authors:  Felix Perez; Ana Minatti
Journal:  Org Lett       Date:  2011-03-25       Impact factor: 6.005

7.  Synthetic Efforts to Investigate the Effect of Planarizing the Triarylamine Geometry in Dyes for Dye-Sensitized Solar Cells.

Authors:  David Moe Almenningen; Veslemøy Minge Engh; Eivind Andreas Strømsodd; Henrik Erring Hansen; Audun Formo Buene; Bård Helge Hoff; Odd Reidar Gautun
Journal:  ACS Omega       Date:  2022-06-16

8.  An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors:  Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Adv Synth Catal       Date:  2012-06-27       Impact factor: 5.837

Review 9.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

10.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457
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