4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent

François Richard; Carlos Mateos; Stellios Arseniyadis

doi:10.1055/s-0040-1706019

SynOpen, Table of Contents

CC BY-NC-ND 4.0 · SynOpen 2021; 05(01): 25-28
DOI: 10.1055/s-0040-1706019

review

4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent

François Richard

^aQueen Mary University of London, School of Biological and Chemical Sciences, London, E1 4NS, UK

,

Carlos Mateos

^bCentro de Investigación Lilly S.A., Avda. de la Industria 30, Alcobendas-Madrid 28108, Spain

,

Stellios Arseniyadis ∗

^aQueen Mary University of London, School of Biological and Chemical Sciences, London, E1 4NS, UK

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor K. C. Nicolaou on the occasion of his 74^th birthday

Abstract

4-Cyano-3-oxotetrahydrothiophene (c-THT) has much more to offer than just a platform to various heterocyclic scaffolds. This solid, bench-stable and commercially available reagent can be readily transformed into thioglycolic acid and acrylonitrile upon simple addition of a hydroxide anion. This interesting feature enables its use as a particularly versatile acrylonitrile anion surrogate.

Key words

acrylonitrile - surrogate - heterocycle - alkylation - Michael addition - palladium - retro-Dieckmann

Full Text

References

References

1a Hergué N, Mallet C, Savitha G, Allain M, Frère P, Roncali J. Org. Lett. 2011; 13: 1762
1b Moussallem C, Olivier S, Grolleau J, Allain M, Mallet C, Savitha G, Gohier F, Frère P. Chem. Eur. J. 2016; 6510

2 Redman AM, Dumas J, Scott WJ. Org. Lett. 2000; 2: 2061
3 Kovács D, Molnár-Tóth J, Blaskó G, Fejes I, Nyerges M. Synth. Commun. 2015; 45: 1675
4 Baraldi PG, Pollini GP, Zanirato V, Barco A, Benetti S. Synthesis 1985; 969
5 Skagseth S, Akhter S, Paulsen MH, Muhammad Z, Lauksund S, Samuelsen Ø, Leiros HK. S, Bayer A. Eur. J. Med. Chem. 2017; 135: 159

6a De Oliveira MN, Arseniyadis S, Cossy J. Chem. Eur. J. 2018; 24: 4810
6b Song T, Arseniyadis S, Cossy J. Org. Lett. 2019; 21: 603
6c Aubert S, Katsina T, Arseniyadis S. Org. Lett. 2019; 21: 2231
6d De Oliveira M.N, Fournier J, Arseniyadis S, Cossy J. Org. Lett. 2017; 19: 14
6e Fournier J, Arseniyadis S, Cossy J. Angew. Chem. Int. Ed. 2012; 51: 7562
6f Fournier J, Lozano O, Menozzi C, Arseniyadis S, Cossy J. Angew. Chem. Int. Ed. 2013; 52: 1257
6g Arseniyadis S, Fournier J, Thangavelu S, Lozano O, Prevost S, Archambeau A, Menozzi C, Cossy J. Synlett 2013; 2350
6h Elhachemia H, Cattoen M, Cordier M, Cossy J, Arseniyadis S, Ilitki H, El Kaïm L. Chem. Commun. 2016; 52: 14490
6i Song T, Arseniyadis S, Cossy J. Chem. Eur. J. 2018; 24: 8076
6j Kerim MD, Cattoen M, Fincias N, Dos Santos A, Arseniyadis S, El Kaïm L. Adv. Synth. Catal. 2018; 360: 449
6k Kerim MD, Katsina T, Cattoen M, Fincias N, Arseniyadis S, El Kaïm L. J. Org. Chem. 2020; 85: 12514

7 Katsina T, Sharma SP, Buccafusca R, Quinn DJ, Moody TS, Arseniyadis S. Org. Lett. 2019; 21: 9348

8a Lauberteaux J, Pichon D, Baslé O, Mauduit M, Marcia de Figueiredo R, Campagne JM. ChemCatChem 2019; 11: 5705
8b Mansot J, Vasseur JJ, Arseniyadis S, Smietana M. ChemCatChem 2019; 11: 5686

9 Duchemin N, Cattoen M, Gayraud O, Anselmi S, Siddiq B, Buccafusca R, Daumas M, Ferey V, Smietana M, Arseniyadis S. Org. Lett. 2020; 22: 5995