Cu(OTf)2-catalyzed multicomponent reactions

Abstract

This review reports the achievements in copper(II) triflate-catalyzed processes concerning the multicomponent reactions, applied to the synthesis of acyclic and cyclic compounds. In particular, for the heteropolycyclic systems mechanistic insights were outlined as well as cycloaddition and aza-Diels-Alder reactions were included. These strategies have gained attention due to their highly atom- and step-economy, one-step multi-bond forming, mild reaction conditions, low cost and easy handling.

Keywords: cascade process; copper catalysis; heteropolycycles; multicomponent reactions; one-pot reaction.

Figure 1

Plausible general catalytic activation for ionic or radical mechanisms.

Scheme 1

Synthesis of α-aminonitriles 1.

Scheme 2

Synthesis of β-amino ketone or β-amino ester derivatives 3.

Scheme 3

Synthesis of 1-(α-aminoalkyl)-2-naphthol derivatives 4.

Scheme 4

Synthesis of thioaminals 5.

Scheme 5

Synthesis of aryl- or amine-containing alkanes 6 and 7.

Scheme 6

Synthesis of 1-aryl-2-sulfonamidopropanes 8.

Scheme 7

Synthesis of α-substituted propargylamines 10.

Scheme 8

Synthesis of N-propargylcarbamates 11.

Scheme 9

Synthesis of (E)-vinyl sulfones 12.

Scheme 10

Synthesis of o-halo-substituted aryl chalcogenides 13.

Scheme 11

Synthesis of α-aminophosphonates 14.

Scheme 12

Synthesis of unsaturated furanones and pyranones 15–17.

Scheme 13

Synthesis of substituted dihydropyrimidines 18.

Scheme 14

Regioselective synthesis of 1,4-dihydropyridines 20.

Scheme 15

Synthesis of tetrahydropyridines 21.

Scheme 16

Synthesis of furoquinoxalines 22.

Scheme 17

Synthesis of 2,4-substituted quinolines 23.

Scheme 18

Synthesis of cyclic ether-fused tetrahydroquinolines 24.

Scheme 19

Practical route for 1,2-dihydroisoquinolines 25.

Scheme 20

Synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives 26.

Scheme 21

Synthesis of polysubstituted pyrroles 27.

Scheme 22

Enantioselective synthesis of polysubstituted pyrrolidines 30 directed by the copper complex 29.

Scheme 23

Synthesis of 4,5-dihydropyrazoles 31.

Scheme 24

Synthesis of 2 arylisoindolinones 32.

Scheme 25

Synthesis of imidazo[1,2-a]pyridines 33.

Scheme 26

Synthesis of isoxazole-linked imidazo[1,2-a]azines 35.

Scheme 27

Synthesis of 2,3-dihydro-1,2,4-triazoles 36.

Scheme 28

Synthesis of naphthopyrans 37.

Scheme 29

Synthesis of benzo[g]chromene derivatives 38.

Scheme 30

Synthesis of naphthalene annulated 2-aminothiazoles 39, piperazinyl-thiazoloquinolines 40 and thiazolocoumarins 41.

Scheme 31

Synthesis of furo[3,4-b]pyrazolo[4,3-f]quinolinones 42.

Scheme 32

Synthesis of spiroindoline-3,4’-pyrano[3,2-b]pyran-4-ones 43.

Scheme 33

Synthesis of N-(α-alkoxy)alkyl-1,2,3-triazoles 44.

Scheme 34

Synthesis of 4-(α-tetrasubstituted)alkyl-1,2,3-triazoles 45.