A novel sequence of Sonogashira coupling and electrophilic addition to an ynone, with concomitant deprotection and cyclocondensation, opens a new one-pot synthesis of 3-halofurans; the method can be readily elaborated to a new sequential Sonogashira–addition–cyclocondensation–Suzuki reaction to furnish 2,3,5-trisubstituted furans in a one-pot fashion.

A consecutive four-component synthesis of highly-substituted tetrahydro-β-carbolines 6 can be achieved by a coupling-aminatio-aza-annulation-Pictet–Spengler (CAAPS) sequence creating five new σ-bonds and four new stereocenters in a one-pot fashion. The structures were unambiguously supported by X-ray structure analyses.

The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straightforward one-pot three component access to enaminones 5 under mild conditions and in excellent yields. Furthermore, 2,4-di- and 2,4,6-trisubstituted pyrimidines 7 can be synthesized in moderate to good yields according to a highly flexible coupling-addition-cyclocondensation sequence.