Preparation of Arylamines, Part 4: From Benzoic Acids and Aryl Ketones

This video is about the conversion of benzoic acid derivatives, aryl ketones, and benzaldehydes into arylamines. These reactions are less common than those discussed in Parts 1, 2, and 3, but can be relevant for certain target compounds. Included are examples of Schmidt, Curtius, Lossen, Hofmann, and Beckmann rearrangements, and also some related, transition-metal catalyzed reactions. Further examples (patents are available at ) Org. Syn. 2014, 91, 27; 2002, 78, 234; J. Am. Chem. Soc. 2023, 145, 32-36; Org. Proc. Res. Dev. 2022, 26, 3312-3322; Synlett 2022, 33, 1468-1472; Synthesis 2022, 54, 5261-5272; J. Org. Chem. 2022, 87, 12653-12672; 11958-11967; 6403-6409; J. Am. Chem. Soc. 2021, 143, 21211-21217; J. Org. Chem. 2021, 86, 2820-2826; 2020, 85, 2476-2485; Synthesis 2020, 52, 2099-2105; 1841-1846; Ang. Chem. Int. Ed. 2019, 58, 892-896; ACS Catal. 2019, 9, 2063-2067; ACS Sust. Chem. Eng. 2019, 7, 6906-6916; Synthesis 2019, 51, 3709-3714; Org. Lett. 2019, 21, 2818-2822; Chem. Sci. 2019, 10, 6661-6671; J. Am. Chem. Soc. 2018, 140, 5264-5271; J. Org. Chem. 2018, 83, 13080-13087; 5816-5824; 2040-2049; Tetrahedron 2018, 74, 5546-5553; Synlett 2018, 29, 1465-1468; 2017, 28, 2594-2598; J. Org. Chem. 2017, 82, 8251-8257; Tetrahedron Lett. 2017, 58, 2298-2301; J. Am. Chem. Soc. 2017, 139, 12153-12156; Synthesis 2016, 48, 1550-1560; ACS Catal. 2016, 6, 969-973; Org. Proc. Res. Dev. 2016, 20, 233-241; J. Org. Chem. 2016, 81, 9372-9380; Org. Lett. 2016, 18, 5560-5563; 2015, 17, 2206-2209; Tetrahedron Lett. 2015, 56, 599-601; Tetrahedron 2015, 71, 700-708; Synthesis 2015, 47, 2971-2975; 1227-1237; Org. Proc. Res. Dev. 2014, 18, 1589-1592; Synlett 2014, 25, 665-670; 2012, 23, 2627-2630; Org. Lett. 2012, 14, 946-949; J. Org. Chem. 2012, 77, 11399-11404; 5364-5370; Tetrahedron 2010, 66, 2132-2140; Org. Lett. 2010, 12, 4644-4647; Synthesis 2010, 3705-3709; 1771-1776; 1104-1106; Org. Lett. 2009, 11, 5622-5625; J. Org. Chem. 2008, 73, 2894-2897; Synthesis 2008, 2589-2593; Tetrahedron 2007, 63, 9007-9015; Org. Lett. 2005, 7, 4107-4110; J. Am. Chem. Soc. 2005, 127, 11240-11241; Org. Proc. Res. Dev. 2002, 6, 759-761.