Esters to Primary Alcohols, Part 3: Boron Hydrides скачать в хорошем качестве

Esters to Primary Alcohols, Part 3: Boron Hydrides

This video is about the reduction of esters to alcohols with boron hydrides, such as alkali borohydrides or diborane. These reducing agents are more expensive than hydrogen or sodium but more selective and easier to handle. Most reductions won't require much optimization, and these reagents are therefore particularly well suited for quick laboratory preparations. Further examples (patents are available at https://worldwide.espacenet.com/): Org. Proc. Res. Dev. 2020, 24, 2890-2897; 2019, 23, 1887-1891; 2018, 22, 1419-1425; 2017, 21, 1602-1609; 2013, 17, 1540-1542 (methanolysis borate esters); 2012, 16, 1854-1860; 2009, 13, 1413-1418 (NaBH4, AlCl3); 478-482; 2007, 11, 918-921 (3-ketoester); 90-93 (monoethyl malonate); 2004, 8, 1072-1075 (acids); 389-395 (malonate); Molecules 2021, 26, 5589 (diester); RSC Advances 2019, 9, 32017-32020 (diester); J. Org. Chem. 2018, 83, 1431-1440 (NaBH4, NaOMe); Org. Lett. 2018, 20, 6444-6448 (ketoester); ACS Catalysis 2018, 8, 3667-3672 (benzylic bromide); Tetrahedron 2018, 74, 336-340 (nitrodiester); J. Am. Chem. Soc. 2016, 138, 5150-5158 (NaBH4, CeCl3); RSC Advances 2016, 6, 85182-85185 (benzylic chloride); Syn. Comm. 2016, 46, 348-354 (diester); Ang. Chem. Int. Ed. Eng. 2015, 54, 5108-5111 (alkyl iodide); Org. Syn. 2012, 89, 420-431; Syn. Comm. 2011, 41, 1276-1281; 2010, 40, 3423-3429 (NaBH4, CeCl3); Synthesis 2009, 660-664 (NaBH4, CoCl2); J. Fluorine Chem. 2008, 129, 848-851 (diester); Tetrahedron Lett. 2008, 49, 1041-1044 (NaBH4, Br2); 2007, 48, 7595-7598 (KBH4, MgCl2); Bioorg. Med. Chem. Lett. 2007, 17, 3736-3740 (benzylic chloride, BH3); ARKIVOC 2006, 1, 128-133; Synlett 2004, 1034-1038 (ketoester); Org. Lett. 2004, 6, 4133-4136 (PTC); Syn. Comm. 2003, 33, 1733-1750 (diglyme, 162 °C); Synlett 2003, 1611-1614 (acrylate); Heterocycles 2003, 59, 101-105 (diester); Bioorg. Med. Chem. 2003, 11, 2739-2749 (diester); Tetrahedron Lett. 2000, 41, 5653-5657 (diester); J. Org. Chem. 2000, 65, 6780-6783 (diester); Tetrahedron Lett. 1997, 38, 1577-1580 (ketoester); 529-532 (LiR2NBH3); Tetrahedron 1997, 53, 5273-5290 (ketoester); J. Org. Chem. 1995, 60, 2968-2973 (NaBH4, AlCl3); Syn. Comm. 1990, 20, 2319-2325 (nitroesters); 1988, 18, 1765-1771; Tetrahedron 1987, 43, 235-242 (ketoester); J. Org. Chem. 1987, 52, 5364-5374 (NaBH4, BF3OEt2, diester); 1982, 47, 4702-4708; 1981, 46, 4584-4585 (PEG); Tetrahedron Lett. 1975, 3295-3296.