Literature DB >> 28464545

Enantioselective Dearomative Difunctionalization of Indoles by Palladium-Catalyzed Heck/Sonogashira Sequence.

Ren-Rong Liu1, Yong-Gang Wang1, Ying-Long Li1, Bing-Bing Huang1, Ren-Xiao Liang1, Yi-Xia Jia1.   

Abstract

Palladium-catalyzed enantioselective dearomative arylalkynylation of N-substituted indoles, through a Heck/Sonogashira sequence, was established using a new BINOL-based phosphoramidite as the chiral ligand. A wide range of 2,3-disubstituted indolines, bearing vicinal quaternary and tertiary stereocenters, were efficiently constructed in one step with excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (>20:1).
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; asymmetric catalysis; dearomatization; heterocycles; palladium

Year:  2017        PMID： 28464545     DOI： 10.1002/anie.201703833

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


  10 in total

1.  Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

Authors:  Conghui Tang; Mikiko Okumura; Yunbo Zhu; Annie R Hooper; Yu Zhou; Yu-Hsuan Lee; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

2.  Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes.

Authors:  Ping Yang; Chao Zheng; Yu-Han Nie; Shu-Li You
Journal:  Chem Sci       Date:  2020-06-10       Impact factor: 9.825

3.  Highly selective Diels-Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole.

Authors:  Carlos H Escalante; Eder I Martínez-Mora; Carlos Espinoza-Hicks; Alejandro A Camacho-Dávila; Fernando R Ramos-Morales; Francisco Delgado; Joaquín Tamariz
Journal:  Beilstein J Org Chem       Date:  2020-06-17       Impact factor: 2.883

4.  Quadruple C-H activation coupled to hydrofunctionalization and C-H silylation/borylation enabled by weakly coordinated palladium catalyst.

Authors:  Bo-Cheng Tang; Wen-Xuan Lin; Xiang-Long Chen; Cai He; Jin-Tian Ma; Yan-Dong Wu; Yu Lan; An-Xin Wu
Journal:  Nat Commun       Date:  2020-11-09       Impact factor: 14.919

5.  Palladium catalyst immobilized on functionalized microporous organic polymers for C-C coupling reactions.

Authors:  Wei Xu; Cijie Liu; Dexuan Xiang; Qionglin Luo; You Shu; Hongwei Lin; Yangjian Hu; Zaixing Zhang; Yuejun Ouyang
Journal:  RSC Adv       Date:  2019-10-28       Impact factor: 4.036

6.  Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles.

Authors:  Ren-Xiao Liang; Ke Wang; Ling-Jie Song; Wei-Jian Sheng; Yi-Xia Jia
Journal:  RSC Adv       Date:  2019-05-07       Impact factor: 3.361

7.  Dearomatization through Photoredox Hydroarylation: Discovery of a Radical-Polar Crossover Strategy.

Authors:  Kelly A McDaniel; Nathan T Jui
Journal:  Org Lett       Date:  2021-07-07       Impact factor: 6.072

8.  Enantioselective palladium/copper-catalyzed C-C σ-bond activation synergized with Sonogashira-type C(sp3)-C(sp) cross-coupling alkynylation.

Authors:  Feng-Na Sun; Wan-Chun Yang; Xiao-Bing Chen; Yu-Li Sun; Jian Cao; Zheng Xu; Li-Wen Xu
Journal:  Chem Sci       Date:  2019-06-21       Impact factor: 9.825

9.  Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues.

Authors:  Cang Cheng; Bin Wan; Bo Zhou; Yichao Gu; Yanghui Zhang
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

Review 10.  Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions.

Authors:  Risto Savela; Carolina Méndez-Gálvez
Journal:  Chemistry       Date:  2021-02-02       Impact factor: 5.236
  10 in total

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