Literature DB >> 31310448

Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Feiyang Xu1, Katerina M Korch1, Donald A Watson1.   

Abstract

For the first time, an aza-Heck cyclization that allows the preparation of indoline scaffolds is described. Using N-hydroxy anilines as electrophiles, which can be easily accessed from the corresponding nitroarenes, this method provides indolines bearing pendant functionality and complex ring topologies. Synthesis of challenging indolines, such as those bearing fully substituted carbon atoms at C2, is also possible using this method.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aza-Heck reaction; catalysis; cyclization; indolines; palladium

Year:  2019        PMID： 31310448      PMCID： PMC6750995          DOI： 10.1002/anie.201907758

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  44 in total

1.  Efficient intramolecular oxidative amination of olefins through direct dioxygen-coupled palladium catalysis.

Authors:  Shannon R Fix; Jodie L Brice; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-04       Impact factor: 15.336

2.  Chasing a phantom by total synthesis: the butylcycloheptylprodigiosin case.

Authors:  Alois Fürstner; Karin Radkowski; Hartwig Peters
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-29       Impact factor: 15.336

3.  Palladium(II)-Catalyzed Cyclization of Olefinic Tosylamides.

Authors:  Richard C. Larock; Timothy R. Hightower; Lisa A. Hasvold; Karl P. Peterson
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

4.  Dichlororuthenium(IV) complex of meso-tetrakis(2,6-dichlorophenyl)porphyrin: active and robust catalyst for highly selective oxidation of arenes, unsaturated steroids, and electron-deficient alkenes by using 2,6-dichloropyridine N-oxide.

Authors:  Jun-Long Zhang; Chi-Ming Che
Journal:  Chemistry       Date:  2005-06-20       Impact factor: 5.236

5.  5-endo Heck-type cyclization of 2-(trifluoromethyl)allyl ketone oximes: Synthesis of 4-difluoromethylene-substituted 1-pyrrolines.

Authors:  Junji Ichikawa; Ryo Nadano; Naotaka Ito
Journal:  Chem Commun (Camb)       Date:  2006-09-13       Impact factor: 6.222

6.  Aerobic intramolecular oxidative amination of alkenes catalyzed by NHC-coordinated palladium complexes.

Authors:  Michelle M Rogers; Johanna E Wendlandt; Ilia A Guzei; Shannon S Stahl
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

7.  Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism and optical rotation: the schizozygane alkaloid schizozygine.

Authors:  Philip J Stephens; Jian-Jung Pan; Frank J Devlin; Marie Urbanová; Josef Hájícek
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

Review 8.  Synthesis of aza-heterocycles from oximes by amino-Heck reaction.

Authors:  Mitsuru Kitamura; Koichi Narasaka
Journal:  Chem Rec       Date:  2002       Impact factor: 6.771

9.  Oxidation of indole substrates by oxodiperoxomolybdenum.trialkyl(aryl)-phosphine oxide complexes.

Authors:  Christine I Altinis Kiraz; Thomas J Emge; Leslie S Jimenez
Journal:  J Org Chem       Date:  2004-03-19       Impact factor: 4.354

10.  A new catalytic hetero-Heck type reaction.

Authors:  Juho Helaja; Richard Göttlich
Journal:  Chem Commun (Camb)       Date:  2002-04-07       Impact factor: 6.222
View more
  6 in total

1.  Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Org Lett       Date:  2021-08-30       Impact factor: 6.072

2.  Radical Aza-Heck Cyclization of Imidates via Energy Transfer, Electron Transfer, and Cobalt Catalysis.

Authors:  Allen F Prusinowski; Henry C Sise; Taylor N Bednar; David A Nagib
Journal:  ACS Catal       Date:  2022-03-28       Impact factor: 13.700

3.  Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades.

Authors:  Benjamin T Jones; Javier García-Cárceles; Lewis Caiger; Ian R Hazelden; Richard J Lewis; Thomas Langer; John F Bower
Journal:  J Am Chem Soc       Date:  2021-09-21       Impact factor: 15.419

4.  Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp3)-H Functionalization Cascades.

Authors:  Changcheng Jing; Benjamin T Jones; Ross J Adams; John F Bower
Journal:  J Am Chem Soc       Date:  2022-09-09       Impact factor: 16.383

5.  Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

Authors:  Run-Duo Gao; Scott A Shuler; Donald A Watson
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825

Review 6.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.