Literature DB >> 28940876

Rapid Assembly of Diversely Functionalized Spiroindenes by a Three-Component Palladium-Catalyzed C-H Amination/Phenol Dearomatization Domino Reaction.

Liangxin Fan1, Jingjing Liu1, Lu Bai1, Yaoyu Wang1, Xinjun Luan1,2.   

Abstract

A novel palladium-catalyzed three-component reaction of phenol-derived biaryls with N-benzoyloxyamines and norbornadiene (NBD) has been developed for the assembly of highly functionalized spiroindenes. This domino process was realized through NBD-assisted C-H amination and phenol dearomatization by forming one C-N bond and two C-C bonds in a single step. Preliminary studies indicated that asymmetric control of this transformation was feasible with chiral ligands. Moreover, the potential synthetic utility of this methodology was highlighted by a series of further transformations.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H amination; dearomatization; homogeneous catalysis; palladium; spiroannulation

Year:  2017        PMID： 28940876     DOI： 10.1002/anie.201708310

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


  6 in total

1.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

2.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

3.  Redox-neutral ortho-C-H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis.

Authors:  Shuqing Chen; Peng Wang; Hong-Gang Cheng; Chihui Yang; Qianghui Zhou
Journal:  Chem Sci       Date:  2019-07-23       Impact factor: 9.825

4.  Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives.

Authors:  Kun Liu; Wenxu Song; Yuqi Deng; Huiyue Yang; Chunlan Song; Takfaoui Abdelilah; Shengchun Wang; Hengjiang Cong; Shan Tang; Aiwen Lei
Journal:  Nat Commun       Date:  2020-01-07       Impact factor: 14.919

5.  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

6.  Pd-Catalyzed Alkene Diamination Reactions with O-Benzoylhydroxylamine Electrophiles: Evidence Supporting a Pd(II/IV) Catalytic Cycle, the Role of 2,4-Pentanedione Derivatives as Ligands, and Expanded Substrate Scope.

Authors:  Janelle K Kirsch; Gabriel A Gonzalez; Mason S Faculak; John P Wolfe
Journal:  J Org Chem       Date:  2021-08-04       Impact factor: 4.198
  6 in total

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