Preparation of Imidazoles, Part 3: From Other Imidazoles by Substitution of Hydrogen

This video is about the chemical transformation of imidazoles by substitution of hydrogen, e.g., halogenation, nitration, acylation, alkylation, arylation, vinylation, metalation, etc.
Further examples (patents are available at worldwide.espa...
Org. Syn. 2015, 92, 342 (quaternization); 2002, 79, 236 (quaternization);
J. Org. Chem. 2024, 89, 1492-1504 (iodination, allylation); ACS Catal. 2024, 14, 6728-6739 (allylation); J. Org. Chem. 2023, 88, 11834-11846 (alkylation); 2655-2665 (allylation); 163-171 (difluoromethylation); Eur. J. Org. Chem. 2023, 26, e202201504 (chlorination); Org. Lett. 2023, 25, 7004-7008 (arylation); J. Org. Chem. 2022, 87, 7202-7212 (nitration); 2021, 86, 4598-4606 (alkylation); 1769-1778 (arylation); Org. Lett. 2021, 23, 1996-2001 (arylation); Synthesis 2021, 53, 3011-3018 (aminocarbonylation); Chem. Sci. 2021, 12, 3890-3897 (aminoalkylation); ACS Omega 2021, 6, 25940-25949 (iodination); J. Am. Chem. Soc. 2020, 142, 1200-1205 (alkylation); Synlett 2020, 31, 179-182 (alkylation); J. Org. Chem. 2019, 84, 13135-13143 (arylation); 4921-4925 (arylation); 792-805; J. Am. Chem. Soc. 2019, 141, 18230-18237 (alkylation); ACS Omega 2018, 3, 3513-3521 (chlorination); Org. Proc. Res. Dev. 2017, 21, 52-59 (N-alkylation); Org. Lett. 2015, 17, 1042-1045 (halogenation); J. Org. Chem. 2015, 80, 8539-8551 (arylation); Tetrahedron Lett. 2012, 53, 7040-7043 (aminocarbonylation); J. Org. Chem. 2012, 77, 9921-9925 (dehalogenation); 8477-8482 (N-alkylation); 3284-3287 (azo coupling); 2011, 76, 8885-8890 (alkylation); 8138-8142 (arylation); 1468-1471 (acylation); Tetrahedron 2011, 67, 8338-8342 (aminocarbonylation); Org. Proc. Res. Dev. 2011, 15, 449-454 (iodination); J. Org. Chem. 2010, 75, 4911-4920 (arylation); 2009, 74, 6371-6373 (N-vinylation); 2200-2202 (arylation); Syn. Comm. 2009, 40, 81-86 (N-alkylation); Org. Biomol. Chem. 2009, 7, 2214-2222 (vinylation); Tetrahedron Lett. 2009, 50, 3463-3466 (alkylation, vinylation); J. Am. Chem. Soc. 2009, 131, 8971-8983 (allylation); Adv. Syn. Catal. 2009, 351, 1268-1272 (arylation); Tetrahedron 2008, 64, 6060-6072 (arylation); J. Med. Chem. 2008, 51, 2944-2953 (halogen-metal exchange, benzylation); J. Org. Chem. 2008, 73, 9121-9124 (N-arylation); 6816-6823 (methylation); 2007, 72, 8543-8546 (arylation); Tetrahedron 2007, 63, 1970-1980 (arylation); Synlett 2006, 18, 3170-3172 (arylation); J. Org. Chem. 2006, 71, 5000-5003 (glycosylation); 2005, 70, 3997-4005 (arylation); Tetrahedron Lett. 2004, 45, 1869-1872 (aminocarbonylation); J. Am. Chem. Soc. 2003, 125, 5274-5275 (arylation); J. Org. Chem. 2003, 68, 4345-4354 (Diels-Alder); Org. Lett. 2002, 4, 4543-4546 (N-vinylation); J. Org. Chem. 2001, 66, 8344-8348 (halogenation); 2000, 65, 4039-4047 (acylation); 1999, 64, 8084-8089 (formylation); Org. Proc. Res. Dev. 1999, 3, 104-108; Synthesis 1995, 1183-1189 (quaternization, alkylation); J. Org. Chem. 1991, 56, 4296-4300 (deiodination).

[@alleau3]

Precise, as always

[@Felixkeeg]

This is an absolute treasure trove. Similar to Science of Synthesis, but I find SoS often quite dated

[@ChemicaLove]

Thanks!