Literature DB >> 30052456

GaCl3-Catalyzed Ring-Opening Carbonyl-Olefin Metathesis.

Haley Albright1, Hannah L Vonesh1, Marc R Becker1, Brandon W Alexander1, Jacob R Ludwig1, Ren A Wiscons1, Corinna S Schindler1.   

Abstract

The development of a Lewis acid-catalyzed ring-opening cross-metathesis reaction which enables selective access to acyclic, unsaturated ketones as the carbonyl-olefin metathesis products is described. While catalytic amounts of FeCl3 were previously identified as optimal to catalyze ring-closing metathesis reactions, the complementary ring-opening metathesis between cyclic alkenes and carbonyl functionalities relies on GaCl3 as the superior Lewis acid catalyst.

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Year:  2018        PMID: 30052456     DOI: 10.1021/acs.orglett.8b02086

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  11 in total

1.  Catalyst Behavior in Metal-Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Carly S Hanson; Mary C Psaltakis; Janiel J Cortes; James J Devery
Journal:  J Am Chem Soc       Date:  2019-07-22       Impact factor: 15.419

2.  Ring-Opening Carbonyl-Olefin Metathesis of Cyclobutenes.

Authors:  Maxwell G Holl; Tristan H Lambert
Journal:  ACS Catal       Date:  2022-04-07       Impact factor: 13.700

3.  Metal-Free Ring-Opening Metathesis Polymerization with Hydrazonium Initiators.

Authors:  Phong K Quach; Jesse H Hsu; Ivan Keresztes; Brett P Fors; Tristan H Lambert
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-13       Impact factor: 16.823

4.  Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy.

Authors:  Carly S Hanson; James J Devery
Journal:  J Vis Exp       Date:  2020-02-20       Impact factor: 1.355

5.  Investigation of Lewis Acid-Carbonyl Solution Interactions via Infrared-Monitored Titration.

Authors:  Carly S Hanson; Mary C Psaltakis; Janiel J Cortes; Sameera S Siddiqi; James J Devery
Journal:  J Org Chem       Date:  2019-12-27       Impact factor: 4.354

6.  Lewis acid-catalyzed carbonyl-olefin metathesis.

Authors:  Paul S Riehl; Corinna S Schindler
Journal:  Trends Chem       Date:  2019-03-15

7.  Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) Homo-Dimers as Lewis Acidic Superelectrophiles.

Authors:  Haley Albright; Paul S Riehl; Christopher C McAtee; Jolene P Reid; Jacob R Ludwig; Lindsey A Karp; Paul M Zimmerman; Matthew S Sigman; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2019-01-16       Impact factor: 15.419

8.  Combined Theoretical and Experimental Investigation of Lewis Acid-Carbonyl Interactions for Metathesis.

Authors:  Tanmay Malakar; Carly S Hanson; James J Devery; Paul M Zimmerman
Journal:  ACS Catal       Date:  2021-03-25       Impact factor: 13.084

Review 9.  Carbonyl-Olefin Metathesis.

Authors:  Haley Albright; Ashlee J Davis; Jessica L Gomez-Lopez; Hannah L Vonesh; Phong K Quach; Tristan H Lambert; Corinna S Schindler
Journal:  Chem Rev       Date:  2021-06-16       Impact factor: 72.087

10.  Catalytic, transannular carbonyl-olefin metathesis reactions.

Authors:  Paul S Riehl; Daniel J Nasrallah; Corinna S Schindler
Journal:  Chem Sci       Date:  2019-09-25       Impact factor: 9.825

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