Literature DB >> 27936302

Highly Site Selective Formal [5+2] and [4+2] Annulations of Isoxazoles with Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines.

Wen-Bo Shen1, Xin-Yu Xiao1, Qing Sun1, Bo Zhou1, Xin-Qi Zhu1, Juan-Zhu Yan1, Xin Lu1, Long-Wu Ye1,2.   

Abstract

Platinum-catalyzed formal [5+2] and [4+2] annulations of isoxazoles with heterosubstituted alkynes enabled the atom-economical synthesis of valuable 1,3-oxazepines and 2,5-dihydropyridines, respectively. Importantly, this Pt catalysis not only led to unique reactivity dramatically divergent from that observed under Au catalysis, but also proceeded via unprecedented α-imino platinum carbene intermediates.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulation; heterocycles; homogeneous catalysis; platinum; ynamides

Year:  2016        PMID： 27936302     DOI： 10.1002/anie.201610042

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


  10 in total

1.  Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Authors:  Peter E Simm; Prakash Sekar; Jeffery Richardson; Paul W Davies
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.084

2.  Facile synthesis of α-alkoxyl amides via scandium-catalyzed oxidative reaction between ynamides and alcohols.

Authors:  Zhi-Xin Zhang; Bo-Han Zhu; Pei-Xi Xie; Jia-Qi Tang; Xin-Ling Li; Chunyin Zhu; Ying-Wu Yin; Long-Wu Ye
Journal:  RSC Adv       Date:  2018-05-18       Impact factor: 4.036

3.  Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

Authors:  Wen-Bo Shen; Qing Sun; Long Li; Xin Liu; Bo Zhou; Juan-Zhu Yan; Xin Lu; Long-Wu Ye
Journal:  Nat Commun       Date:  2017-11-23       Impact factor: 14.919

4.  Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations.

Authors:  Sovan Sundar Giri; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

5.  Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors:  Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336

6.  Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement.

Authors:  RahulKumar Rajmani Singh; Manisha Skaria; Liang-Yu Chen; Mu-Jeng Cheng; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-11-12       Impact factor: 9.825

7.  Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate.

Authors:  Antony Sekar Kulandai Raj; Kuo-Chen Tan; Liang-Yu Chen; Mu-Jeng Cheng; Rai-Shung Liu
Journal:  Chem Sci       Date:  2019-05-22       Impact factor: 9.825

8.  Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

Authors:  Bo Zhou; Ying-Qi Zhang; Kairui Zhang; Ming-Yang Yang; Yang-Bo Chen; You Li; Qian Peng; Shou-Fei Zhu; Qi-Lin Zhou; Long-Wu Ye
Journal:  Nat Commun       Date:  2019-07-19       Impact factor: 14.919

9.  Dichotomy of platinum(II) and gold(III) carbene intermediates switching from N- to O-selectivity.

Authors:  Hongming Jin; Wen-Yan Tong; Jing Zhang; Matthias Rudolph; Frank Rominger; Xu Shen; Shuanglin Qu; A Stephen K Hashmi
Journal:  Nat Commun       Date:  2022-03-30       Impact factor: 14.919

10.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336
  10 in total

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