Literature DB >> 27144944

Palladium(0)-Catalyzed Intermolecular Carbocyclization of (1,n)-Diynes and Bromophenols: An Efficient Route to Tricyclic Scaffolds.

Lu Bai1, Yini Yuan1, Jingjing Liu1, Jiaoyu Wu1, Lingbo Han1, Hui Wang1, Yaoyu Wang1, Xinjun Luan2,3.   

Abstract

A novel palladium(0)-catalyzed dearomative cyclization reaction of bromophenols with (1,n)-diynes has been developed for building two new types of tricyclic architectures containing a quaternary carbon center. This method employs inexpensive bromophenols, and easily accessible tethered diynes. It exhibits a broad substrate scope and tolerates various functional groups. Preliminary results with commercially available chiral ligands indicate that enantioselective variants are feasible for both cyclization processes.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; arenes; cyclizations; dearomatization; palladium

Year:  2016        PMID: 27144944     DOI: 10.1002/anie.201601570

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


  5 in total

1.  Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

Authors:  Chao Ning; Kang-Hua Rui; Yin Wei; Min Shi
Journal:  Chem Sci       Date:  2022-06-01       Impact factor: 9.969

2.  Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence.

Authors:  Zi-Lei Xia; Chao Zheng; Ren-Qi Xu; Shu-Li You
Journal:  Nat Commun       Date:  2019-07-17       Impact factor: 14.919

3.  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

4.  Two-in-one strategy for fluorene-based spirocycles via Pd(0)-catalyzed spiroannulation of o-iodobiaryls with bromonaphthols.

Authors:  Bojun Tan; Long Liu; Huayu Zheng; Tianyi Cheng; Dianhu Zhu; Xiaofeng Yang; Xinjun Luan
Journal:  Chem Sci       Date:  2020-09-08       Impact factor: 9.825

5.  Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet-Hauser rearrangement.

Authors:  Chongqing Pan; Wenjing Guo; Zhenhua Gu
Journal:  Chem Sci       Date:  2018-06-14       Impact factor: 9.825

  5 in total

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