Gold Catalysis and Furans: A Powerful Match for Synthetic Connections

Abstract

This review summarizes the advances made on the synthesis and functionalization of furans via gold catalysis during the period between 2016 and 2020. A separate section is dedicated to the tandem gold-catalyzed synthesis and functionalization of furans.1 Introduction2 Gold-Catalyzed Synthesis of Furans2.1 Cycloisomerizations of Alkynyl and Cumulenyl Alcohols2.2 Cycloisomerizations of Alkynyl and Allenyl Ketones2.3 Reactions with External Oxidants2.4 Miscellaneous3 Gold-Catalyzed Functionalization of Furans3.1 Cycloadditions3.2 Furan Ring Decorations3.3 Reactions Involving Furan Ring Opening4 Gold-Catalyzed Tandem Synthesis and Functionalization of Furans­4.1 Cycloisomerizations Followed by Gold-Catalyzed Cycloaddition4.2 Cycloisomerizations to a Gold 1,3- or 1,4-Dipole and Intermolecular Annulation4.3 Cycloisomerizations to a Gold Carbene and Intermolecular Trapping5 Conclusion

Alcohol Dehydrogenases and N‐Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β‐Disubstituted Allylic Alcohols

“…This is in accordance with the already described reactivity of furan derivatives in combination with gold catalysis,o ccurring e.g.,f uran-alkyne intramolecular cyclizations or other rearrangements. [58] At this point, the use of pyridine derivatives was omitted since it is well known that the basic nitrogen atom coordinates to the gold catalyst leading to adramatic loss of the metal activity, [59] requiring therefore higher reaction temperatures [60] that on the other hand would not be compatible with as econd enzymatic reaction.…”

Gold(i)-catalyzed diastereo- and enantioselective [4 + 3] cycloadditions: construction of functionalized furano-benzoxepins

“…1 Thus, tremendous efforts have been devoted to the efficient construction of furan derivatives, including the traditional Paal–Knorr reactions, metal-catalyzed protocols and metal-free strategies. 2,3 In this context, the development of expedient and facile methods for the preparation of functionalized substituted furans, especially those bearing multiple stereocenters, is synthetically appealing but highly challenging in organic synthesis.…”

Transformation of 3-(Furan-2-yl)-1,3-di(het)arylpropan-1-ones to Prop-2-en-1-ones via Oxidative Furan Dearomatization/2-Ene-1,4,7-triones Cyclization

“…Furosemide is a potent loop diuretic that is used for edema secondary to congestive heart failure exacerbation, liver and kidney failure, and high blood pressure [ 14 , 15 ]. Moreover, due to their versatile reactivity, furans are intensively used in organic synthesis as universal building blocks for the preparation of various useful products, including natural compounds [ 16 , 17 , 18 , 19 , 20 ].…”