Literature DB >> 26293968

Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles.

Michael J James1, Rosa E Clubley1, Kleopas Y Palate1, Thomas J Procter1, Anthony C Wyton1, Peter O'Brien1, Richard J K Taylor1, William P Unsworth1.   

Abstract

A high-yielding, divergent approach to generate either spirocyclic indolenines or carbazoles from a common indole-tethered propargyl alcohol precursor is described, with mechanistic insight provided. Either product can be obtained upon treatment with different Ag(I) catalysts at rt. An unexpected hydration reaction to afford (±)-actinopolymorphol B is also reported.

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Year:  2015        PMID： 26293968     DOI： 10.1021/acs.orglett.5b02216

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


  6 in total

1.  From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis.

Authors:  Sarah J Chambers; Graeme Coulthard; William P Unsworth; Peter O'Brien; Richard J K Taylor
Journal:  Chemistry       Date:  2016-03-23       Impact factor: 5.236

2.  A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines.

Authors:  Nantachai Inprung; Michael J James; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2021-03-01       Impact factor: 6.005

3.  Selectivity, Speciation, and Substrate Control in the Gold-Catalyzed Coupling of Indoles and Alkynes.

Authors:  Ryan G Epton; William P Unsworth; Jason M Lynam
Journal:  Organometallics       Date:  2022-02-10       Impact factor: 3.876

4.  Cu(i)-catalyzed cross-coupling of primary amines with 2,2'-dibromo-1,1'-biphenyl for the synthesis of polysubstituted carbazole.

Authors:  Yan-Ning Niu; Yan Qiao; Ke-Yu Wang; Bai-Xue Sha; Gao-Qiang Li
Journal:  RSC Adv       Date:  2022-08-25       Impact factor: 4.036

5.  Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.

Authors:  John T R Liddon; Michael J James; Aimee K Clarke; Peter O'Brien; Richard J K Taylor; William P Unsworth
Journal:  Chemistry       Date:  2016-05-19       Impact factor: 5.236

6.  Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.

Authors:  James A Rossi-Ashton; Aimee K Clarke; James R Donald; Chao Zheng; Richard J K Taylor; William P Unsworth; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336
  6 in total

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