Literature DB >> 27442021

Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes To Synthesize Indolenines with C3-Quarternary Centers.

Shang Gao1, Zijun Wu1, Xinxin Fang1, Aijun Lin1, Hequan Yao1.   

Abstract

A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C-H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.

Entities:  

Year:  2016        PMID: 27442021     DOI: 10.1021/acs.orglett.6b01947

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors:  Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

Review 2.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

3.  A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes.

Authors:  Ding-Wei Ji; Yan-Cheng Hu; Hao Zheng; Chao-Yang Zhao; Qing-An Chen; Vy M Dong
Journal:  Chem Sci       Date:  2019-05-16       Impact factor: 9.825

4.  Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.

Authors:  Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi
Journal:  Chem Sci       Date:  2018-05-11       Impact factor: 9.825

5.  Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch.

Authors:  Cecilia Ciccolini; Giacomo Mari; Francesco G Gatti; Giuseppe Gatti; Gianluca Giorgi; Fabio Mantellini; Gianfranco Favi
Journal:  J Org Chem       Date:  2020-08-21       Impact factor: 4.354

6.  A Concise Total Synthesis of the Fungal Isoquinoline Alkaloid TMC-120B.

Authors:  Ahmad K Haidar; Niels D Kjeldsen; Nikolaj S Troelsen; Viola Previtali; Kasper P Lundquist; Thomas O Larsen; Mads H Clausen
Journal:  Molecules       Date:  2022-01-14       Impact factor: 4.411

  6 in total

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