Literature DB >> 21517088

Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Huijun Dong1, Regina T Latka, Tom G Driver.   

Abstract

A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.

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Year:  2011        PMID： 21517088      PMCID： PMC3097088          DOI： 10.1021/ol2008268

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


  54 in total

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Authors:  Mark S Taylor; Eric N Jacobsen
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2.  Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

Authors:  Erika Milczek; Nadège Boudet; Simon Blakey
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3.  A general copper-catalyzed coupling of azoles with vinyl bromides.

Authors:  Qian Liao; Yuxing Wang; Liyun Zhang; Chanjuan Xi
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

4.  Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors:  Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

5.  Recent advances in transition metal-catalyzed N-atom transfer reactions of azides.

Authors:  Tom G Driver
Journal:  Org Biomol Chem       Date:  2010-07-08       Impact factor: 3.876

Review 6.  Understanding and exploiting C-H bond activation.

Authors:  Jay A Labinger; John E Bercaw
Journal:  Nature       Date:  2002-05-30       Impact factor: 49.962

7.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

8.  Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

Authors:  Benjamin J Stokes; Brankica Jovanović; Huijun Dong; Kathleen J Richert; Ryan D Riell; Tom G Driver
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

9.  Synthesis and biological evaluation of novel gamma-carboline analogues of Dimebon as potent 5-HT6 receptor antagonists.

Authors:  Alexandre V Ivachtchenko; Eugene B Frolov; Oleg D Mitkin; Volodymyr M Kysil; Alexander V Khvat; Ilya M Okun; Sergey E Tkachenko
Journal:  Bioorg Med Chem Lett       Date:  2009-05-03       Impact factor: 2.823

10.  Synthesis of beta- and gamma-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes.

Authors:  Haiming Zhang; Richard C Larock
Journal:  J Org Chem       Date:  2002-10-04       Impact factor: 4.354
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  4 in total

1.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source.

Authors:  Quyen Nguyen; Ke Sun; Tom G Driver
Journal:  J Am Chem Soc       Date:  2012-04-24       Impact factor: 15.419

3.  Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

Authors:  Quyen Nguyen; Tuyen Nguyen; Tom G Driver
Journal:  J Am Chem Soc       Date:  2013-01-03       Impact factor: 15.419

4.  Synthesis of Structurally Diverse 2,3-Fused Indoles via Microwave-Assisted AgSbF6-Catalysed Intramolecular Difunctionalization of o-Alkynylanilines.

Authors:  Yuanqiong Huang; Yan Yang; Hongjian Song; Yuxiu Liu; Qingmin Wang
Journal:  Sci Rep       Date:  2015-08-27       Impact factor: 4.379
  4 in total

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