Preparation of Alkynes, Part 5: By Acylation, Carboxylation, and Cyanation of Terminal Alkynes

This video is about the acylation, carboxylation, and cyanation of terminal alkynes for the preparation of ynones, propiolic acid derivatives, and cyanoalkynes. At the end you'll find a discussion of the many potential side reactions, including the addition of nucleophiles to these highly electrophilic products.
Further examples (patents are available at worldwide.espa...
Org. Syn. 2008, 85, 88 (iminium triflate); 1987, 65, 47 (ClCO2Me); 1986, 64, 108 (ClCO2Et); 1981, 60, 81 (ClCO2Me); 1962, 42, 97 (carboxylation);
Organometallics 2023, 42, 362-371 (carboxylation); J. Org. Chem. 2023, 88, 7219-7227 (aminocarbonylation); J. Org. Chem. 2021, 86, 1850-1860 (carboxylation); J. Am. Chem. Soc. 2021, 143, 12460-12466 (arylcarbonylation); ACS Appl. Nano Mat. 2021, 4, 7107-7115 (carboxylation); ACS Catal. 2020, 10, 831-841 (acylation, ArCHO); Org. Biomol. Chem. 2020, 18, 9216-9220 (cyanation); Chem. Eur. J. 2019, 25, 10366-10374 (cyanation); J. CO2 Utilization 2019, 32, 140-145 (carboxylation); J. Org. Chem. 2019, 84, 16116-16123 (acylation, RCOCl); ACS Appl. Mat. Interf. 2019, 11, 28858-28867 (carboxylation); Tetrahedron Lett. 2018, 59, 4622-4625 (cyanation); ACS Sust. Chem. Eng. 2017, 5, 9634-9639 (carboxylation); Org. Lett. 2017, 19, 5613-5616 (cyanation); Inorg. Chem. 2017, 56, 3414-3420 (carboxylation); ACS Catal. 2015, 5, 3940-3944 (carboxylation); J. Org. Chem. 2015, 80, 9314-9320 (radical acylation); Org. Lett. 2015, 17, 3054-3057 (radical acylation); 920-923 (acylation, ArCHO); 2014, 16, 4174-4177 (carbonylation); 488-491 (acylation, RCOCl); J. Org. Chem. 2013, 78, 3676-3687 (acylation); Synlett 2013, 24, 1269-1274 (acylation, RCN); ACS Catal. 2012, 2, 2014-2021 (carboxylation); Org. Lett. 2011, 13, 2402-2405 (carboxylation); 944-947 (arylcarbonylation); J. Am. Chem. Soc. 2010, 132, 11926-11928 (acylation); Ang. Chem. Int. Ed. 2008, 47, 9700-9703 (formylation, isonitrile); Org. Lett. 2006, 8, 689-692 (acylation, RCOCl); J. Org. Chem. 2005, 70, 6126-6128 (acylation, RCOCl); Chem. Comm. 2005, 634-636 (formylation, isonitrile); J. Am. Chem. Soc. 2004, 126, 10860-10861 (formylation, isonitrile); J. Org. Chem. 2002, 67, 5032-5035 (acylation, Weinreb); Org. Proc. Res. Dev. 2002, 6, 308-310 (carboxylation, ClCO2Bn); Chem. Lett. 2001, 30, 1210-1211 (acylation, RCOSiR3); J. Org. Chem. 1999, 64, 313-315 (cyanation).