Preparation of Carboxylic Acids, Part 6: Carbonylation

This video is about the preparation of carboxylic acids by carbonylation with carbon monoxide. You'll find examples of the carbonylation of alcohols, alkanes, carbocations, phenyllithium, aryl bromides, aryl chlorides, benzyl bromides, allylic chlorides, alkyl chlorides, alkyl bromides, epoxides, vinyl sulfonates, alkenes, alkynes, and arenes. At the end of the video there are some examples of the more critical potential side reactions.
Further examples (patents are available at worldwide.espa...)
Org. Syn. 2020, 97, 125 (HCO2R, Pd); 2015, 92, 237 (ArBr, Pd); 2009, 86, 287 (epoxide, Cr, Co); 1990, 69, 114 (BuLi); 1966, 46, 72 (ROH, HCO2H); 1964, 44, 69 (oxalyl chloride);
Org. Proc. Res. Dev. 2020, 24, 2665-2675 (ArBr, Pd); 713-723 (Pd); 2019, 23, 1669-1673 (Rh, Cu); 2018, 22, 1745-1752 (MeOH to AcOH, Rh); 499-505 (Pd); 2011, 15, 717-720 (Pd, flow); 2009, 13, 634-637 (ArI, Pd); 2008, 12, 566-574; 2003, 7, 429-431 (ArN2X, Pd); 2002, 6, 677-681 (ArN2BF4, Pd); 2001, 5, 572-574; 1998, 2, 366-378 (BnBr);
Coord. Chem. Rev. 2023, 475, 214900 (review); Tetrahedron 2023, 133, 133292 (RI, Pd); Ang. Chem. Int. Ed. 2023, 62, e202213297 (Ni); J. Org. Chem. 2023, 88, 5153-5160 (ArI, Pd); 5127-5134 (ArI, Pd); 5078-5089 (ArBr, Pd); 882-892 (diene, Pd); Catalysts 2022, 12, 883 (ROH, Pd); Chem. Comm. 2022, 58, 9312-9327 (review); 4643-4646 (Ni); Organometallics 2022, 41, 2903-2908 (ArOTf, Pd); 2021, 40, 674-681 (R3B); Org. Lett. 2021, 23, 5164-5169 (oxalyl chloride); 3939-3943 (alkene, Ru); Synlett 2021, 32, 7-13; 2020, 31, 788-792 (R3Al, RNCO); 369-372 (BnCl, Pd); Organometallics 2020, 39, 1881-1886 (ROH, Pd); 870-880 (Ni); ChemCatChem 2019, 11, 997-1001 (ArCl, Pd); Org. Lett. 2019, 21, 6919-6923 (RPyBF4, Co); 2518-2522 (ArSMe2OTf, Pd); J. Org. Chem. 2019, 84, 16076-16085 (RI, Pd); ACS Catal. 2019, 9, 6987-6992 (Cu); 5897-5901; 5545-5551 (Rh); J. Am. Chem. Soc. 2018, 140, 7979-7993 (ArCl, Pd); J. Org. Chem. 2017, 82, 2319-2328 (Pd); 1105-1113 (CHCl3, Pd); ACS Catal. 2017, 7, 6089-6093 (styrene, Pd); Synlett 2017, 28, 835-840 (ArI, Pd); 2016, 27, 1854-1859 (AgNO3); J. Am. Chem. Soc. 2016, 138, 7520-7523 (Pd); J. Org. Chem. 2016, 81, 5256-5262 (Pd); 3860-3867 (alkene); 2015, 80, 7547-7554 (CHCl3, Pd); 7126-7133 (alkyne, Co); 1920-1928 (ArBr, Pd); J. Am. Chem. Soc. 2015, 137, 8556-8563 (allene, Pd); Org. Lett. 2015, 17, 2832-2835 (oxalyl chloride); Synthesis 2015, 47, 1861-1868 (ArHal, Pd); 2014, 46, 1689-1708 (Pd); Acc. Chem. Res. 2014, 47, 1563-1574 (Pd, RI); J. Org. Chem. 2014, 79, 12191-12196 (alkene, Ru); Synlett 2014, 25, 1241-1245 (ArBr, Pd); 2013, 24, 1848-1850 (RBr, Pd); ACS Catal. 2013, 3, 287-293 (ArI, Pd); J. Org. Chem. 2013, 78, 1547-1552 (chloroketone, Pd); Tetrahedron 2013, 69, 11197-11202 (alkyne, Co); J. Am. Chem. Soc. 2013, 135, 2891-2894 (ArHal, Pd); 2012, 134, 17696-17703 (Pd); Synthesis 2012, 423-430 (allyl alcohol, Pd); Synlett 2012, 23, 1331-1334 (RI, Pd); J. Org. Chem. 2012, 77, 6155-6165 (ArI, Pd); 4793-4800 (RLi); 3793-3799 (ArX, Pd); 2008-2012 (ArI, Pd); 2011, 76, 5489-5494 (ArBr, Pd); J. Am. Chem. Soc. 2010, 132, 8858-8859 (Au); 686-693 (Pd); J. Org. Chem. 2010, 75, 8410-8415 (ArCl, Mo); 3017-3020 (ArBr, Mo, W); 2009, 74, 8332-8335 (ArHal, Pd); 888-890 (alkene, Pd); J. Am. Chem. Soc. 2008, 130, 9429-9433 (ArIn); J. Org. Chem. 2007, 72, 9630-9634 (epoxide, Co); 567-573 (epoxide, Co); Synlett 2007, 2537-2540 (ArOTf, Pd); Synthesis 2006, 3106-3110 (ArBr, Pd); 3003-3008 (allyl-OTs, alkyne, Pd); Synlett 2005, 3154-3156 (RI); J. Org. Chem. 2005, 70, 3094-3098 (ArBr, Pd); 2244-2249 (RI, light); 2004, 69, 4356-4360 (RI, light); 2003, 68, 3558-3562 (ArOTf, Pd); 2002, 67, 7014-7018 (Ru); 6232-6235 (ArBr, Pd); 2001, 66, 6229-6233 (diene, Pd); 2000, 65, 254-255 (oxalyl chloride); 1999, 64, 9201-9205 (ArI, Pd); 2080-2084 (alkyne, Pd); J. Chem. Soc. Perk II 1976, 1895-1901 (RMgX); Bull. Chem. Soc. Jpn. 1971, 44, 2001 (SbCl5, RHal); Tetrahedron 1960, 10, 55-64 (RH, AlCl3).

[@ChemicaLove]

Always excited to see new Florencio uploads!

[@synthesiswithflorenciozara1848]

thank you! more are on the way (in 3 months or so), probably about alkenes.