Literature DB >> 22753504

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones.

Timothy J Donohoe1, Ben S Pilgrim, Geraint R Jones, José A Bassuto.   

Abstract

The utilization of sequential palladium-catalyzed α-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.

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Year:  2012        PMID： 22753504      PMCID： PMC3406859          DOI： 10.1073/pnas.1206532109

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  33 in total

1.  Concise synthesis of isoquinoline via the Ugi and Heck reactions.

Authors:  Zheng Xiang; Tuoping Luo; Kui Lu; Jiayue Cui; Xiaomeng Shi; Reza Fathi; Jiahua Chen; Zhen Yang
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

2.  The azaallylic anion as a synthon for pd-catalyzed synthesis of heterocycles: domino two- and three-component synthesis of indoles.

Authors:  José Barluenga; Agustín Jiménez-Aquino; Carlos Valdés; Fernando Aznar
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

Authors:  Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

4.  Nickel-catalyzed addition of pyridine-N-oxides across alkynes.

Authors:  Kyalo Stephen Kanyiva; Yoshiaki Nakao; Tamejiro Hiyama
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Synthesis of 3,4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: total synthesis of coralydine.

Authors:  Manon Chaumontet; Riccardo Piccardi; Olivier Baudoin
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  A multicomponent reaction of arynes, isocyanides, and terminal alkynes: highly chemo- and regioselective synthesis of polysubstituted pyridines and isoquinolines.

Authors:  Feng Sha; Xian Huang
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.

Authors:  Fabio Bellina; Renzo Rossi
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

8.  Isoquinoline synthesis via rhodium-catalyzed oxidative cross-coupling/cyclization of aryl aldimines and alkynes.

Authors:  Nicolas Guimond; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

9.  Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging Suzuki coupling reactions.

Authors:  Thomas J Colacot; Helene A Shea
Journal:  Org Lett       Date:  2004-10-14       Impact factor: 6.005

10.  Assembly of isoquinolines via CuI-catalyzed coupling of beta-keto esters and 2-halobenzylamines.

Authors:  Bao Wang; Biao Lu; Yongwen Jiang; Yihua Zhang; Dawei Ma
Journal:  Org Lett       Date:  2008-05-29       Impact factor: 6.005
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  9 in total

Review 1.  Direct Asymmetric Alkylation of Ketones: Still Unconquered.

Authors:  Rafael Cano; Armen Zakarian; Gerard P McGlacken
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

2.  Late-Stage Diversification: A Motivating Force in Organic Synthesis.

Authors:  Kelly E Kim; Alexia N Kim; Carter J McCormick; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2021-10-06       Impact factor: 16.383

3.  Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines.

Authors:  Alexia N Kim; Aurapat Ngamnithiporn; Eric R Welin; Martin T Daiger; Christian U Grünanger; Michael D Bartberger; Scott C Virgil; Brian M Stoltz
Journal:  ACS Catal       Date:  2020-02-10       Impact factor: 13.084

4.  Short and efficient syntheses of protoberberine alkaloids using palladium-catalyzed enolate arylation.

Authors:  Alice E Gatland; Ben S Pilgrim; Panayiotis A Procopiou; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-27       Impact factor: 15.336

5.  Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles.

Authors:  Harish K Potukuchi; Anatol P Spork; Timothy J Donohoe
Journal:  Org Biomol Chem       Date:  2015-04-21       Impact factor: 3.876

6.  Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.

Authors:  Ben S Pilgrim; Alice E Gatland; Charlie T McTernan; Panayiotis A Procopiou; Timothy J Donohoe
Journal:  Org Lett       Date:  2013-11-19       Impact factor: 6.005

7.  Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.

Authors:  Fei Zhou; Tom G Driver
Journal:  Org Lett       Date:  2014-05-27       Impact factor: 6.005

8.  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Authors:  Enrico Marelli; Martin Corpet; Yury Minenkov; Rifahath M Neyyappadath; Alessandro Bismuto; Giulia Buccolini; Massimiliano Curcio; Luigi Cavallo; Steven P Nolan
Journal:  ACS Catal       Date:  2016-03-30       Impact factor: 13.084

9.  Activating group recycling in action: a rhodium-catalyzed carbothiolation route to substituted isoquinolines.

Authors:  Milan Arambasic; Joel F Hooper; Michael C Willis
Journal:  Org Lett       Date:  2013-10-01       Impact factor: 6.005
  9 in total

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