Gold(I)-Catalyzed Intramolecular C(sp3)–H Bond Functionalization

Rubén Miguélez; Omar Arto; Carlos Rodríguez-Arias; Pablo Barrio

doi:10.1055/a-2389-7434

Synthesis, Table of Contents

Synthesis 2025; 57(06): 1138-1152
DOI: 10.1055/a-2389-7434

short review

Special Topic Dedicated to Prof. Erick Carreira

Gold(I)-Catalyzed Intramolecular C(sp3)–H Bond Functionalization

Rubén Miguélez‡

,

Omar Arto‡

,

Carlos Rodríguez-Arias‡

,

Pablo Barrio∗

Abstract

All articles of this category

Dedicated to Prof. Carreira on the occasion of his 60^th birthday

Abstract

The merger of two of the most rapidly growing fields in catalysis, namely gold-catalysis and C–H activation/functionalization has resulted in major breakthroughs, affording unprecedented transformations. This review covers the most relevant contributions in this field during the last 10 years, restricted to the intramolecular functionalization of C(sp³)–H bonds.

1 Introduction

2 Carbene/Vinylidene Insertion

3 [1,5]-H Shift

4 Gold-Stabilized Vinyl Cation Mediated

5 Summary and Outlook

Key words

gold-catalysis - C–H functionalization - cyclization - carbene insertion - [1,5]-hydride shift - vinyl cation

Full Text

References

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For recent examples, see:

70a Zhao F, Abdellaoui M, Hagui W, Ballarin-Marion M, Berthet J, Corcé V, Delbaere S, Dossmann H, Espagne A, Forté J, Jullien L, Le Saux T, Mouriès-Mansuy V, Ollivier C, Fensterbank L. Nat. Commun. 2022; 13: 2295
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71 Miguélez R, Semleit N, Rodríguez-Arias C, Mykhailiuk P, González JM, Haberhauer G, Barrio P. Angew. Chem. Int. Ed. 2023; 62: e202305296
72 For a recent review on the synthesis of the cyclopentene core, see: Miguélez R, Barrio P, González JM. Chem. Rec. 2023; 23: e202300254
73 For a synthetic application of the obtained 1-bromocyclopentene derivatives, see: Miguélez R, Arto O, Rodríguez-Arias C, del Blanco A, Barrio P, González JM. Eur. J. Org. Chem. 2024; 27: e202301274
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75 Recently, a propargyl C–H functionalization with the intermediacy of a gold allenylidene has been disclosed: Wei Y, Jiang J, Jing Y, Ke Z, Zhang L. Angew. Chem. Int. Ed. 2024; 63: e202402286