Preparation of Alkynes, Part 2: By Alkylation of Terminal Alkynes

This video is about the alkylation of terminal alkynes for the preparation of internal alkynes. You'll find here examples with full experimental details of alkylations under alkaline, neutral, and acidic reaction conditions, and a discussion of potential side reactions.
Further examples (patents are available at worldwide.espa...
Org. Syn. 2008, 85, 118 (aldehyde, In); 2007, 84, 120 (MeCHO, Li); 2005, 81, 157 (HCHO, Li); 2002, 79, 27 (epoxide, Li); 1990, 69, 120 (HCHO, Li); 1990, 68, 14 (ketone, Li); 1977, 57, 26 (bromide, Na); 1970, 50, 97 (bromide, Mg); 1959, 39, 56 (aldehyde, Mg); 1952, 32, 70 (ketone); 1950, 30, 15 (bromide, Na); 1949, 29, 47 (ketone); 1940, 20, 40 (acetone);
Org. Lett. 2023, 25, 7095-7099 (Michael, Cu); 4514-4519 (triflate, Cu); J. Org. Chem. 2023, 88, 7755-7763 (ketone, Co, Zn); 1194-1199 (Cu, Zn); 2022, 87, 1554-1558 (Fe); J. Am. Chem. Soc. 2022, 144, 14828-14837; Molecules 2022, 27, 3088 (review, Cu); Org. Lett. 2022, 24, 5186-5191; 2021, 23, 8169-8173 (Cu); 3190-3194 (Zn); 129-134 (Cu); J. Am. Chem. Soc. 2021, 143, 17983-17988 (Ts-hydrazone, Cu); Chem. Comm. 2021, 57, 7529-7532 (bromide, Li); J. Org. Chem. 2020, 85, 8723-8731 (Ag); Synlett 2020, 31, 60-64 (aldehyde, Zn); Org. Lett. 2020, 22, 5456-5461 (Cu); 2019, 21, 7655-7659 (ketone, Li); Synlett 2018, 29, 185-188 (Mannich, Zn); J. Am. Chem. Soc. 2018, 140, 6006-6013 (radicals); ACS Catal. 2017, 7, 6872-6876 (Cu); Org. Lett. 2017, 19, 2378-2381 (Michael); 1934-1937 (fluoride, Al); 743-745 (aldehyde, Zn); 2016, 18, 2982-2985 (Cu); 2040-2043 (Michael, Cu); Chem. Eur. J. 2016, 22, 2787-2792; Chem. Soc. Rev. 2015, 44, 8124-8173 (review, Ag); Org. Lett. 2015, 17, 1684-1687 (oxidative Mannich); 198-201 (HCHO, Zn); Synlett 2012, 23, 2758-2762 (ketone, Ag); J. Org. Chem. 2012, 77, 1251-1257 (CF3, Cu); Org. Proc. Res. Dev. 2011, 15, 570-580 (Michael, Mg); J. Am. Chem. Soc. 2011, 133, 17142-17145 (Cu); Adv. Syn. Catal. 2010, 352, 1446-1450 (Cu); J. Am. Chem. Soc. 2010, 132, 10275-10277 (Michael, Cu); 7262-7263 (CF3, Cu); 5186-5192 (acrolein, Zn); Org. Proc. Res. Dev. 2009, 13, 331-335; Org. Lett. 2009, 11, 1701-1704 (oxidative Mannich); Chem. Comm. 2008, 35-48 (enolate alkynylation); Org. Lett. 2007, 9, 165-167 (Mannich, Ag); J. Org. Chem. 2007, 72, 9590-9596 (ketone, Rh); Chem. Comm. 2006, 4263-4275 (Mannich); Org. Lett. 2006, 8, 879-881 (ROH); J. Org. Chem. 2005, 70, 5733-5736 (ketone, Zn); Chem. Comm. 2004, 1638-1639 (Mannich); Org. Lett. 2004, 6, 2281-2283 (Michael, Zn); J. Am. Chem. Soc. 2003, 125, 6054-6055 (Michael, Cu); Org. Lett. 2002, 4, 2605-2606 (aldehyde, Zn); J. Am. Chem. Soc. 2001, 123, 9687-9688 (aldehyde, Zn); Org. Lett. 2001, 3, 2089-2091 (Michael, Ru); Ang. Chem. Int. Ed. 1999, 38, 1463-1465 (ketone, CsOH); J. Am. Chem. Soc. 1999, 121, 11245-11246 (Mannich, Zn).

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