Synlett 2023; 34(01): 23-28
DOI: 10.1055/s-0042-1753142
account

A Twenty-Year Survey in Low-Valent Cobalt-Catalyzed Transformations Comes to an End – A Farewell

Gerhard Hilt


Abstract

In this Account, I report the start of my independent career, concerning cobalt-catalyzed carbon–carbon bond formations and the twenty-year long journey to the final decision to abandon the field. Some highlights, such as the regiodiverse neutral Diels–Alder reaction and the cobalt versus ruthenium-catalyzed Alder-ene reaction are discussed. Besides such highlights, also some aspects that led to unpleasant experiences are reported from a personal point of view.

1 Introduction

2 The Regiodivergent Neutral-Diels–Alder Reaction

3 The Chemoselective [2+2+2] Cyclotrimerization of Alkynes and Nitriles

4 The Cobalt-Catalyzed Alder-ene Reaction

5 The Isomerization of Carbon–Carbon Double Bonds

6 The Final Chord

7 Conclusion



Publication History

Received: 18 October 2022

Accepted after revision: 27 October 2022

Article published online:
23 November 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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      Shortly after I started my independent career in Munich in September 1999, my PhD advisor Prof. Eberhard Steckhan passed away so-to-say in the lecture hall in early 2000 and, under shock, we submitted our first paper on cobalt catalysis as soon as possible to a formerly high-ranked journal, see:
    • 3a Hilt G, du Mesnil F.-X. Tetrahedron Lett. 2000; 41: 6757

    • But, I made the same mistake again, see:
    • 3b Hilt G, Korn TJ. Tetrahedron Lett. 2001; 42: 2783
    • 4a Hess W, Treutwein J, Hilt G. Synthesis 2008; 3537
    • 4b Röse P, Hilt G. Synthesis 2016; 48: 463
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    • For early reports, see:
    • 6a Zakharkin LI, Petrushkina EA. J. Org. Chem. USSR 1984; 20: 441
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  • 7 For the synthesis of the moenocinol side-chain, see: Hilt G, Treutwein J. Chem. Commun. 2009; 1395
  • 8 Hilt G, Janikowski J, Hess W. Angew. Chem. Int. Ed. 2006; 45: 5204
  • 9 Fan Q, Wang C, Han Y, Zhu J, Hieringer W, Kuttner J, Hilt G, Gottfried JM. Angew. Chem. Int. Ed. 2013; 52: 4668
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  • 15 Weber SM, Hilt G. Org. Lett. 2017; 19: 564
  • 16 For a review on ruthenium-catalyzed reactions, see: Trost BM, Frederiksen MU, Rudd MT. Angew. Chem. Int. Ed. 2005; 44: 6630
  • 17 For the synthesis of credneramides, see: Erver F, Hilt G. J. Org. Chem. 2012; 77: 5215
  • 18 For the synthesis of urushiol, see: Schmidt A, Hilt G. Chem. Asian J. 2014; 9: 2407
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  • 20 For the correction of reference 19, see: Pünner F, Schmidt A, Hilt G. Angew. Chem. Int. Ed. 2019; 58: 17103
  • 21 Schmidt A, Nödling AR, Hilt G. Angew. Chem. Int. Ed. 2015; 54: 801
  • 22 For eternity unpublished results
  • 23 Surprisingly, a Web of Science search for Prof. Donald Hilvert in association with the key word ‘cobalt’ gave not a single hit?!
  • 24 Over the process of preparing this Account, I had a brief discourse with the editor-in-charge and he sent me a very useful comment for many situations in life. Prof. K. Peter C. Vollhardt wrote in German: ‘Schwamm drüber!’, which translates most likely into: ‘No hard feelings!’ The German metaphor is much more illustrative.