Literature DB >> 24653670

Silver-Promoted Benzannulations of Siloxy Alkynes with Pyridinium and Isoquinolinium Salts.

Jaime R Cabrera-Pardo1, David I Chai1, Sergey A Kozmin1.   

Abstract

We describe the development of efficient benzannulations of siloxy alkynes with pyridinium and isoquinolinium salts. Such reactions are successfully promoted by a stoichiometric amount of silver(I) benzolate under mild reaction conditions. This process proceeds via a formal inverse-electron demand Diels-Alder reaction, followed by fragmentation of the initially produced bicyclic adducts to deliver a range of synthetically useful phenols and naphthols.

Entities:  

Keywords:  alkynes; benzannulation; cycloaddition; silver

Year:  2013        PMID： 24653670      PMCID： PMC3956059          DOI： 10.1002/adsc.201300443

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  8 in total

1.  Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives.

Authors:  S Saito; Y Yamamoto
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  Reactions of (trialkylsilyl)vinylketenes with lithium ynolates: a new benzannulation strategy.

Authors:  Wesley F Austin; Yongjun Zhang; Rick L Danheiser
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

3.  Silver-catalyzed formal inverse electron-demand Diels-Alder reaction of 1,2-diazines and siloxy alkynes.

Authors:  Yunus E Türkmen; Timothy J Montavon; Sergey A Kozmin; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

4.  A novel tandem [2 + 2] cycloaddition-Dieckmann condensation with ynolate anions. Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n + 1] cycloaddition.

Authors:  M Shindo; Y Sato; K Shishido
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

5.  AuBr(3)-catalyzed [4 + 2] benzannulation between an enynal unit and enol.

Authors:  Naoki Asao; Haruo Aikawa; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

6.  AuCl(3)-catalyzed benzannulation: synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes.

Authors:  Naoki Asao; Kumiko Takahashi; Sunyoung Lee; Taisuke Kasahara; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2002-10-30       Impact factor: 15.419

7.  Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes.

Authors:  Naoki Asao; Tsutomu Nogami; Sunyoung Lee; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

8.  Label-assisted mass spectrometry for the acceleration of reaction discovery and optimization.

Authors:  Jaime R Cabrera-Pardo; David I Chai; Song Liu; Milan Mrksich; Sergey A Kozmin
Journal:  Nat Chem       Date:  2013-03-31       Impact factor: 24.427
  8 in total
  2 in total

1.  Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes.

Authors:  An Wu; Hui Qian; Wanxiang Zhao; Jianwei Sun
Journal:  Chem Sci       Date:  2020-07-06       Impact factor: 9.825

2.  Non-precious metals catalyze formal [4 + 2] cycloaddition reactions of 1,2-diazines and siloxyalkynes under ambient conditions.

Authors:  Chintan S Sumaria; Yunus E Türkmen; Viresh H Rawal
Journal:  Org Lett       Date:  2014-06-09       Impact factor: 6.005
  2 in total

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