Literature DB >> 12946157

Green protocol for conjugate addition of thiols to alpha,beta-unsaturated ketones using a [bmim]PF6/H2O system.

J S Yadav1, B V S Reddy, Gakul Baishya.   

Abstract

Alpha,beta-unsaturated ketones undergo conjugate addition rapidly with thiols in a hydrophobic ionic liquid [bmim]PF(6)/H(2)O solvent system (2:1) in the absence of any acid catalyst to afford the corresponding Michael adducts in high to quantitative yields with excellent 1,4-selectivity under mild and neutral conditions. The enones show enhanced reactivity in ionic liquids, thereby reducing reaction times and improving the yields significantly. The use of ionic liquids helps to avoid the use of either acid or base catalysts for this conversion. The recovered ionic liquid was reused four to five times with consistent activity.

Entities:  

Year:  2003        PMID: 12946157     DOI: 10.1021/jo034335l

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  L-proline catalyzed Michael additions of thiophenols to alpha,beta-unsaturated compounds, particularly alpha-enones, in the ionic liquid [bmim]PF6.

Authors:  Peter Kotrusz; Stefan Toma
Journal:  Molecules       Date:  2006-03-17       Impact factor: 4.411

2.  DABCO-catalyzed Knoevenagel condensation of aldehydes with ethyl cyanoacetate using hydroxy ionic liquid as a promoter.

Authors:  Dan Meng; Yongsheng Qiao; Xin Wang; Wei Wen; Sanhu Zhao
Journal:  RSC Adv       Date:  2018-08-28       Impact factor: 3.361

3.  Eliminating Transition State Calculations for Faster and More Accurate Reactivity Prediction in Sulfa-Michael Additions Relevant to Human Health and the Environment.

Authors:  Piers A Townsend; Elliot H E Farrar; Matthew N Grayson
Journal:  ACS Omega       Date:  2022-07-21

4.  Design, Syntheses, and Bioevaluations of Some Novel N2-Acryloylbenzohydrazides as Chemostimulants and Cytotoxic Agents.

Authors:  Kinjal Lakhani; Edgar A Borrego; Karla G Cano; Jonathan R Dimmock; Renato J Aguilera; Swagatika Das; Praveen K Roayapalley; Rajendra K Sharma; Umashankar Das
Journal:  Medicines (Basel)       Date:  2021-06-03
  4 in total

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