Literature DB >> 10823199

Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride.

T Iwama1, V B Birman, S A Kozmin, V H Rawal.   

Abstract

[formula: see text] A new, regiocontrolled synthesis of carbocycle-fused indoles has been developed. The two-step procedure involves first the regiospecific arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride (1). Reduction of the nitro group on the aromatic ring with TiCl3 followed by spontaneous condensation of the aniline with the ketone then affords the indole products.

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Year:  1999        PMID： 10823199     DOI： 10.1021/ol990759j

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


  10 in total

1.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

Authors:  Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal:  J Am Chem Soc       Date:  2019-12-27       Impact factor: 15.419

2.  Enantioselective α-arylation of carbonyls via Cu(I)-bisoxazoline catalysis.

Authors:  James S Harvey; Scott P Simonovich; Christopher R Jamison; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2011-08-17       Impact factor: 15.419

3.  Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.

Authors:  Tetsuo Iwama; Viresh H Rawal
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

4.  Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.

Authors:  Anna E Allen; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2011-03-09       Impact factor: 15.419

5.  Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.

Authors:  Adam M Levinson
Journal:  Org Lett       Date:  2014-08-29       Impact factor: 6.005

6.  A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

Authors:  Linlin Qin; Bao Hu; Kiel D Neumann; Ethan J Linstad; Katelyenn McCauley; Jordan Veness; Jayson J Kempinger; Stephen G DiMagno
Journal:  European J Org Chem       Date:  2015-08-14

7.  Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.

Authors:  Fei Zhou; Tom G Driver
Journal:  Org Lett       Date:  2014-05-27       Impact factor: 6.005

8.  Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group.

Authors:  Tingting Chen; Gang Wang; Lin Tang; Hongpeng Yang; Jing Xu; Xiaoxue Wen; Yunbo Sun; Shuchen Liu; Tao Peng; Shouguo Zhang; Lin Wang
Journal:  Molecules       Date:  2022-03-29       Impact factor: 4.411

9.  Arylation with unsymmetrical diaryliodonium salts: a chemoselectivity study.

Authors:  Joel Malmgren; Stefano Santoro; Nazli Jalalian; Fahmi Himo; Berit Olofsson
Journal:  Chemistry       Date:  2013-06-20       Impact factor: 5.236

10.  A counteranion triggered arylation strategy using diaryliodonium fluorides.

Authors:  L Chan; A McNally; Q Y Toh; A Mendoza; M J Gaunt
Journal:  Chem Sci       Date:  2014-11-12       Impact factor: 9.825
  10 in total

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