The coupling-isomerization reaction is an unusual outcome of the Sonogashira coupling of propargyl alcohols, N-tosylamines, or ethers with preferentially electron-deficient (hetero)aryl halides. As a result, chalcones, enimines and allenyl ethers are generated in situ. The former two are readily transformed into heterocycles in consecutive cyclization and cyclocondensations in a one-pot fashion, whereas the latter are excellent entries into pericyclic domino processes for the rapid construction of complex polycyclic scaffolds. 1 Introduction 2 Michael Systems by Coupling-Isomerization Reactions (CIR) 2.1 EWG-Substituted Propenones by CIR 2.2 EWG-Substituted Propenimines by CIR 2.3 General Microwave-Assisted Coupling-Isomerization Reaction (MACIR) 3 Multicomponent Synthesis of Heterocycles by CIR-Cyclocondensation Sequences 3.1 Pyrazolines by CIR-Cyclocondensation Sequence 3.2 Pyrimidines by CIR-Cyclocondensation Sequence 3.3 Benzoheteroazepines by CIR-Cyclocondensation Sequence 3.4 Furans and Pyrroles by CIR-Stetter-Cyclocondensation Sequences 3.4.1 1,4-Diketones by CIR-Stetter Sequence 3.4.2 Furans by CIR-Stetter-Cyclocondensation Sequence 3.4.3 Pyrroles by CIR-Stetter-Cyclocondensation Sequence 3.5 Annelated and Substituted Pyridines by CIR-Cycloaddition-Cyclocondensation Sequence 3.6 Annelated and Substituted Pyridines by CIR-Cycloaddition Sequence 4 Domino Syntheses Initiated by CIR 4.1 CIR Domino Syntheses of 2-Substituted Quinolines 4.2 CIR-Diels-Alder Domino Syntheses of Polycyclic Skeletons 4.3 Mechanistic Dichotomies in CIR Domino Syntheses 5 Conclusions