Literature DB >> 19180173

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

Wesley F Austin1, Yongjun Zhang, Rick L Danheiser.   

Abstract

(Trialkylsilyl)vinylketenes react with lithium ynolates to generate 3-(oxido)dienylketenes which undergo rapid 6π-electrocyclization. The ultimate products of this benzannulation are highly substituted resorcinol monosilyl ethers which are formed via a [1,3] carbon to oxygen silyl group shift. Further transformations of the benzannulation products are described providing efficient access to ortho-benzoquinones and benzofuran, benzoxepine, and benzoxocine ring systems.

Entities:  

Year:  2008        PMID： 19180173      PMCID： PMC2350204          DOI： 10.1016/j.tet.2007.10.113

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

1.  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

2.  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

3.  Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of alpha,beta-unsaturated delta-valerolactones and -lactams.

Authors:  D M Bennett; I Okamoto; R L Danheiser
Journal:  Org Lett       Date:  1999-08-26       Impact factor: 6.005

4.  Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with alpha-benzotriazolyl organolithium compounds.

Authors:  Christopher P Davie; Rick L Danheiser
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-12       Impact factor: 15.336

5.  Stereoselective [4 + 1] annulation reactions with silyl vinylketenes derived from Fischer carbene complexes.

Authors:  William H Moser; Laura A Feltes; Liangdong Sun; Matthew W Giese; Ryan W Farrell
Journal:  J Org Chem       Date:  2006-08-18       Impact factor: 4.354

6.  Determination of the overlapping pKa values of resorcinol using UV-visible spectroscopy and DFT methods.

Authors:  S E Blanco; M C Almandoz; F H Ferretti
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2005-01-01       Impact factor: 4.098

7.  Novel highly regioselective VO(acac)2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones.

Authors:  Alessandra Lattanzi; Antonello Senatore; Antonio Massa; Arrigo Scettri
Journal:  J Org Chem       Date:  2003-05-02       Impact factor: 4.354

8.  Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and base.

Authors:  Nabi A Magomedov; Piero L Ruggiero; Yuchen Tang
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

9.  Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

10.  Synthesis of highly substituted cyclopentenones via the [4 + 1] cycloaddition of nucleophilic carbenes and vinyl ketenes.

Authors:  James H Rigby; Zhengqiang Wang
Journal:  Org Lett       Date:  2003-02-06       Impact factor: 6.005
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  5 in total

1.  Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C-H silylation of phenols with traceless acetal directing groups.

Authors:  Parham Asgari; Udaya Sree Dakarapu; Hiep H Nguyen; Junha Jeon
Journal:  Tetrahedron       Date:  2016-12-08       Impact factor: 2.457

2.  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

3.  Benzyne Cascade Reactions via Benzoxetenonium Ions and Their Rearrangements to o-Quinone Methides.

Authors:  Hang Shen; Xiao Xiao; Thomas R Hoye
Journal:  Org Lett       Date:  2019-03-04       Impact factor: 6.005

4.  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

5.  α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions.

Authors:  Asmund Kaupang; Tore Bonge-Hansen
Journal:  Beilstein J Org Chem       Date:  2013-07-11       Impact factor: 2.883
  5 in total

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