N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes

N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes

A N-heterocyclic carbene (NHC) catalyzed addition reaction of 3-trimethylsilyl propiolate with aldehydes has been developed. Under the catalysis of 2 mol% NHCs, benzaldehyde, furfural, β-naphthaldehyde, meta- and para-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford...

Full description

Bibliographic Details
Main Authors:	Guang-Fen Du, Xiao-Lei Zou, Bin Dai, Lin He
Format:	Article
Language:	English
Published:	Elsevier 2016-03-01
Series:	Journal of Saudi Chemical Society
Subjects:	N-heterocyclic carbenes 3-Trimethylsilyl propiolate Alkynylation β-Branched Morita–Baylis–Hillman adducts
Online Access:	http://www.sciencedirect.com/science/article/pii/S1319610314000076

Similar Items

Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol
by: Francisco José Seixas Xavier, et al.
Published: (2016-11-01)

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
by: Soundararajan Karthikeyan, et al.
Published: (2020-07-01)

Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
by: Utpal Das, et al.
Published: (2012-03-01)

Methyl 8-oxo-2-phenyl-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate
by: Ralph C. Gomes, et al.
Published: (2016-06-01)

Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols
by: Ahlem Abidi, et al.
Published: (2016-11-01)

Brucine Diol-Catalyzed Enantioselective Morita-Baylis-Hillman Reaction in the Presence of Brucine N-Oxide
by: Venkatachalam Angamuthu, et al.
Published: (2021-02-01)

Easy Access to Evans’ Oxazolidinones. Stereoselective Synthesis and Antibacterial Activity of a New 2-Oxazolidinone Derivative
by: Gaspar Diaz, et al.
Published: (2014-06-01)

Synthesis of 16 New Hybrids from Tetrahydropyrans Derivatives and Morita˗Baylis˗Hillman Adducts: In Vitro Screening against Leishmania donovani
by: Suervy Canuto de Oliveira Sousa, et al.
Published: (2017-01-01)

Enantioselective, Organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman Reactions: Stereochemical Issues
by: José M. Saá, et al.
Published: (2010-02-01)

A Convenient One-Pot Preparation of 2-Methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman Adducts and Their Oxidation to the Corresponding Sulfones
by: Ching-Fa Yao, et al.
Published: (2012-05-01)

Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family
by: Raquel Mato, et al.
Published: (2022-01-01)

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates
by: Olfa Mhasni, et al.
Published: (2023-09-01)

The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry
by: Verónica Carrasco-Sanchez, et al.
Published: (2009-10-01)

Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions
by: Yue, Xiaoyang, et al.
Published: (2021-09-01)

Morita-Baylis-Hillman and Rauhut-Currier Reactions of Conjugated Nitroalkenes
by: Kirandeep Kaur, et al.
Published: (2012-12-01)

Regioselective SN2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
by: Silong Xu, et al.
Published: (2014-04-01)

A Facile and Mild Synthesis of Trisubstituted Allylic Sulfones from Morita-Baylis-Hillman Carbonates
by: Lin Jiang, et al.
Published: (2015-05-01)

Amberlyst A21 catalyzed Morita-Baylis-Hillman reaction
by: Yiheyis Bogale, et al.
Published: (2021-01-01)

Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides
by: Hong-Ping Deng, et al.
Published: (2012-07-01)

Highly Efficient Asymmetric Morita–Baylis–Hillman Reaction Promoted by Chiral Aziridine-Phosphines
by: Aleksandra Buchcic-Szychowska, et al.
Published: (2022-03-01)

Dihydroquinolines, Dihydronaphthyridines and Quinolones by Domino Reactions of Morita-Baylis-Hillman Acetates
by: Joel K. Annor-Gyamfi, et al.
Published: (2021-02-01)

Naphthalenes and Quinolines by Domino Reactions of Morita–Baylis–Hillman Acetates
by: Joel K. Annor-Gyamfi, et al.
Published: (2020-11-01)

Synthesis and Characterization with Computational Studies of Metal Complexes of Methyl 2-((4-cyanophenyl)(hydroxy) methyl)acrylate: A New Biologically Active Multi-Functional Adduct
by: Shazia Ishfaq, et al.
Published: (2022-10-01)

<i>N</i>-Heterocyclic Carbene Adducts of Alkynyl Functionalized 1,3,2-Dithioborolanes
by: Richard Böser, et al.
Published: (2019-04-01)

A Review on Generation and Reactivity of the <i>N</i>-Heterocyclic Carbene-Bound Alkynyl Acyl Azolium Intermediates
by: Ziyang Dong, et al.
Published: (2022-11-01)

N-Heterocyclic carbene catalyzed radical coupling of aldehydes with redox-active esters
by: Song, Runjiang, et al.
Published: (2020)

One-Electron Reduction Potentials: Calibration of Theoretical Protocols for Morita–Baylis–Hillman Nitroaromatic Compounds in Aprotic Media
by: Amauri Francisco da Silva, et al.
Published: (2018-08-01)

Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins
by: Hang Zhang, et al.
Published: (2012-08-01)

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement
by: Siyu Wang, et al.
Published: (2021-10-01)

Facile and innovative catalytic protocol for intramolecular Friedel–Crafts cyclization of Morita–Baylis–Hillman adducts: Synergistic combination of chiral (salen)chromium(III)/BF3·OEt2 catalysis
by: Karthikeyan Soundararajan, et al.
Published: (2021-08-01)

N-Heterocyclic carbenes in synthesis /
by: Nolan, Steven P.
Published: (2006)

N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate
by: Gamze KOZ, et al.
Published: (2023-12-01)

N-heterocyclic carbene catalyzed synthesis of dimethyl carbonate via transesterification of ethylene carbonate with methanol
by: Guang-Fen Du, et al.
Published: (2015-01-01)

Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid
by: Vladimir Lamm, et al.
Published: (2013-04-01)

Synthesis and Elimination Pathways of 1-Methanesulfonyl-1,2-dihydroquinoline Sulfonamides
by: Ebenezer Ametsetor, et al.
Published: (2023-04-01)

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters
by: Lin Yan, et al.
Published: (2013-09-01)

N-Heterocyclic carbene-catalyzed remote enantioselective C-C bond formation via 1,6-addition with formyl enynes
by: Peng, Xiaolin, et al.
Published: (2024)

Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
by: Changgong Xu, et al.
Published: (2021-06-01)

An isatin aldol adduct as a precursor to α,α’-difunctionalized methyl vinyl ketones
by: Ajit Kumar Jha, et al.
Published: (2022-01-01)

Reactions of nitroxides XIII: Synthesis of the Morita–Baylis–Hillman adducts bearing a nitroxyl moiety using 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl as a starting compound, and DABCO and quinuclidine as catalysts
by: Jerzy Zakrzewski
Published: (2012-09-01)