Literature DB >> 22607029

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

Yunus E Türkmen1, Timothy J Montavon, Sergey A Kozmin, Viresh H Rawal.   

Abstract

A highly effective silver-catalyzed formal inverse electron-demand Diels-Alder reaction of 1,2-diazines and siloxy alkynes has been developed. The reactions provide ready access to a wide range of siloxy naphthalenes and anthracenes, which are formed in good to high yields, under mild reaction conditions, using low catalyst loadings.

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Year:  2012        PMID： 22607029      PMCID： PMC3415592          DOI： 10.1021/ja302537j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  21 in total

1.  Synthesis of 2-naphthols via carbonylative Stille coupling reaction of 2-bromobenzyl bromides with tributylallylstannane followed by the Heck reaction.

Authors:  Yao Dai; Xiujuan Feng; Hesong Liu; Hua Jiang; Ming Bao
Journal:  J Org Chem       Date:  2011-11-21       Impact factor: 4.354

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

Review 3.  BINOL: a versatile chiral reagent.

Authors:  Jean Michel Brunel
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

Review 4.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

5.  Silver-catalyzed hydroamination of siloxy alkynes.

Authors:  Jianwei Sun; Sergey A Kozmin
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-24       Impact factor: 15.336

Review 6.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

7.  Lewis-base adducts of 9,10-dihydro-9,10-diboraanthracene: ditopic hydroboration reagents and a B-N analogue of triptycene.

Authors:  Andreas Lorbach; Michael Bolte; Hans-Wolfram Lerner; Matthias Wagner
Journal:  Chem Commun (Camb)       Date:  2010-04-08       Impact factor: 6.222

8.  A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates.

Authors:  Wesley F Austin; Yongjun Zhang; Rick L Danheiser
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

9.  Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropones.

Authors:  Pingfan Li; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

10.  Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes.

Authors:  Liming Zhang; Sergey A Kozmin
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419
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  10 in total

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

Authors:  Jaime R Cabrera-Pardo; David I Chai; Sergey A Kozmin
Journal:  Adv Synth Catal       Date:  2013-09-16       Impact factor: 5.837

2.  Stacks and clips: Uncanny similarities in the modes of self-assembly in tenary Ag(I) complexes with 1,2-diazines and chelating heteroarenes.

Authors:  Yunus E Türkmen; Saikat Sen; Viresh H Rawal
Journal:  CrystEngComm       Date:  2013-06-07       Impact factor: 3.545

3.  Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding.

Authors:  Zixi Zhu; Christopher M Glinkerman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2020-11-30       Impact factor: 15.419

4.  Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2016-09-14       Impact factor: 15.419

5.  [2+2+2] Cycloadditions of siloxy alkynes with 1,2-diazines: from reaction discovery to identification of an antiglycolytic chemotype.

Authors:  Timothy J Montavon; Yunus E Türkmen; Noumaan A Shamsi; Christopher Miller; Chintan S Sumaria; Viresh H Rawal; Sergey A Kozmin
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-07       Impact factor: 15.336

6.  Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels-Alder/Substitution Reaction.

Authors:  Sebastian Beeck; Sebastian Ahles; Hermann A Wegner
Journal:  Chemistry       Date:  2021-12-07       Impact factor: 5.020

7.  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

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

9.  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

10.  Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis.

Authors:  Zhen Cao; Aline Lacoudre; Cybille Rossy; Brigitte Bibal
Journal:  Beilstein J Org Chem       Date:  2019-10-17       Impact factor: 2.883
  10 in total

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