Literature DB >> 26696541

Theoretical study of the mechanism of the N-heterocyclic carbene-catalyzed cyclotetramerization of acrylates.

Dehui Chang1, Qiaoqiao Yang1, Meng Li2, Ran Fang3.   

Abstract

A theoretical study of the N-heterocyclic carbene (NHC)-catalyzed cyclotetramerization of acrylates forming trisubstituted cyclopentenones indicates a mechanism through a key deoxy-Breslow intermediate generated from one molecule of NHC and two molecules of methyl acrylate (MA). Pathways involving different proton-transfer (α or β) and the role of a tert-butoxide ( (t) BuO(-)) group were investigated.

Entities:  

Keywords:  Acrylates; Cyclotetramerization; Density functional theory; N-heterocyclic carbene; Reaction mechanism

Year:  2015        PMID： 26696541     DOI： 10.1007/s00894-015-2884-x

Source DB:  PubMed          Journal:  J Mol Model        ISSN： 0948-5023            Impact factor:   1.810


  22 in total

1.  Conjugate-addition organopolymerization: rapid production of acrylic bioplastics by N-heterocyclic carbenes.

Authors:  Yuetao Zhang; Eugene Y-X Chen
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-23       Impact factor: 15.336

Review 2.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

3.  N-heterocyclic carbenes as organocatalysts.

Authors:  Nicolas Marion; Silvia Díez-González; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  N-Heterocyclic carbene-catalyzed cyclotetramerization of acrylates.

Authors:  Shin-ichi Matsuoka; Shoko Namera; Atsushi Washio; Koji Takagi; Masato Suzuki
Journal:  Org Lett       Date:  2013-11-15       Impact factor: 6.005

5.  Cyclodimerization versus polymerization of methyl methacrylate induced by N-heterocyclic carbenes: a combined experimental and theoretical study.

Authors:  Winnie Nzahou Ottou; Damien Bourichon; Joan Vignolle; Anne-Laure Wirotius; Fredéric Robert; Yannick Landais; Jean-Marc Sotiropoulos; Karinne Miqueu; Daniel Taton
Journal:  Chemistry       Date:  2014-03-06       Impact factor: 5.236

6.  N-heterocyclic carbene catalyzed [4+2] cycloaddition of nitroalkenes with oxodienes.

Authors:  Xiang-Yu Chen; Li-Hui Sun; Song Ye
Journal:  Chemistry       Date:  2013-02-28       Impact factor: 5.236

Review 7.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

8.  N-heterocyclic carbene catalyzed aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines.

Authors:  Lin He; Teng-Yue Jian; Song Ye
Journal:  J Org Chem       Date:  2007-08-18       Impact factor: 4.354

9.  Recent advances in carbon-carbon bond-forming reactions involving homoenolates generated by NHC catalysis.

Authors:  Vijay Nair; Sreekumar Vellalath; Beneesh Pattoorpadi Babu
Journal:  Chem Soc Rev       Date:  2008-10-21       Impact factor: 54.564

10.  Experimental mechanistic studies of the tail-to-tail dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene.

Authors:  Terumasa Kato; Yoshiya Ota; Shin-ichi Matsuoka; Koji Takagi; Masato Suzuki
Journal:  J Org Chem       Date:  2013-08-23       Impact factor: 4.354
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