Abstract
Heterocycles are the largest family of organic compounds due to their wide applications as therapeutic agents, synthetic intermediates, scaffolds, building blocks or fine chemicals. Heterocyclic compounds have been used in material science, biotechnology, pharmaceutical, and agrochemical industries. In the past few years, the use of transition metal complexes, especially palladium, as heterogeneous catalysts has become a trend for synthesising various organic compounds. Pd-catalyzed reactions have been proven to be effective for synthesising a variety of heterocyclic compounds, which are a popular class of molecules in the chemical study. Hence, in this review, we have discussed the palladium-catalyzed synthesis of various heterocyclic compounds, i.e., furan, indole, quinoline, coumarin, and some other heterocycle derivatives.
Keywords: Palladium catalyst, furan, indole, quinolone, coumarin, heterocycles
Graphical Abstract
[http://dx.doi.org/10.1021/cr0306790] [PMID: 15137807]
[http://dx.doi.org/10.2174/1570179043366611]
[http://dx.doi.org/10.1080/00397911.2012.760131]
[http://dx.doi.org/10.1080/00397911.2013.813550]
[http://dx.doi.org/10.1021/cr0505728] [PMID: 16402771]
[http://dx.doi.org/10.1055/s-2003-40507]
[http://dx.doi.org/10.1021/cr900005n]] [PMID: 19438203];
b) Lyons, T.W.; Sanford, M.S. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem. Rev., 2010, 110(2), 1147-1169.
[http://dx.doi.org/10.1021/cr900184e]] [PMID: 20078038];
c) Yeung, C.S.; Dong, V.M. Catalytic dehydrogenative cross-coupling: Forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds. Chem. Rev., 2011, 111(3), 1215-1292.
[http://dx.doi.org/10.1021/cr100280d] [PMID: 21391561]
[http://dx.doi.org/10.1038/446391a]] [PMID: 17377575];
b) Alberico, D.; Scott, M.E.; Lautens, M. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem. Rev., 2007, 107(1), 174-238.
[http://dx.doi.org/10.1021/cr0509760]] [PMID: 17212475];
c) Ackermann, L.; Vicente, R.; Kapdi, A.R. Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage. Angew. Chem. Int. Ed. Engl., 2009, 48(52), 9792-9826.
[http://dx.doi.org/10.1002/anie.200902996] [PMID: 19998294]
[http://dx.doi.org/10.1039/C9RA03563J]
[http://dx.doi.org/10.1016/j.bmcl.2009.03.161] [PMID: 19395261]
[http://dx.doi.org/10.1016/S0040-4039(00)80581-X]
[http://dx.doi.org/10.1021/ja00130a003]
[http://dx.doi.org/10.3987/COM-96-7469]
[http://dx.doi.org/10.1021/jo00034a004]
[http://dx.doi.org/10.1016/S0040-4039(96)01486-4]
[http://dx.doi.org/10.1016/S0040-4020(02)00534-3]
[http://dx.doi.org/10.1016/S0040-4039(00)85084-4]
[http://dx.doi.org/10.1021/jo962386v]
[http://dx.doi.org/10.1021/ja00117a011]
[http://dx.doi.org/10.1002/(SICI)1099-0690(199905)1999:5<1137:AID-EJOC1137>3.0.CO;2-8]
[http://dx.doi.org/10.1021/ol9900764] [PMID: 16118867]
[http://dx.doi.org/10.1016/S0040-4039(98)00231-7]
[http://dx.doi.org/10.1002/chem.200204664] [PMID: 12794889]
[http://dx.doi.org/10.1021/acs.joc.6b02864] [PMID: 28170259]
[http://dx.doi.org/10.1039/a703305b]
[http://dx.doi.org/10.1021/ol034644y] [PMID: 12841750]
[http://dx.doi.org/10.3390/catal8040136]
[http://dx.doi.org/10.3390/molecules23102450] [PMID: 30257438]
[http://dx.doi.org/10.1055/s-1999-2639]
[http://dx.doi.org/10.1016/S0040-4020(01)91149-4]
[http://dx.doi.org/10.1016/S0040-4020(01)01060-2]
[http://dx.doi.org/10.1016/S0040-4039(97)10502-0]
[http://dx.doi.org/10.1021/jo200317f] [PMID: 21542613]
[http://dx.doi.org/10.1021/ol0342812] [PMID: 12713310]
[http://dx.doi.org/10.1002/anie.201210217] [PMID: 23526675]
[http://dx.doi.org/10.1021/jo961051a]
[http://dx.doi.org/10.1021/jo010839c] [PMID: 11925257]
[http://dx.doi.org/10.1039/C9RA00796B]
[http://dx.doi.org/10.1055/s-1993-22360]
[http://dx.doi.org/10.1021/ol0260425] [PMID: 12074667]
[http://dx.doi.org/10.1021/ja203335u] [PMID: 21609019]
[http://dx.doi.org/10.1055/s-2002-20464]
[http://dx.doi.org/10.1016/S0040-4020(01)00774-8]
[http://dx.doi.org/10.1021/jo00126a037]
[http://dx.doi.org/10.1021/ja105366u] [PMID: 20715820]
[http://dx.doi.org/10.1016/S0040-4039(02)02333-X]
[http://dx.doi.org/10.1016/S0040-4020(03)00588-X]
[http://dx.doi.org/10.1021/ol8028687] [PMID: 19199489]
[http://dx.doi.org/10.1021/jo9020634] [PMID: 19842675]
[http://dx.doi.org/10.1016/j.tetlet.2009.06.016]
[http://dx.doi.org/10.1039/C8CC09369E] [PMID: 30724297]
[http://dx.doi.org/10.1039/D1CC06803B] [PMID: 35018924]
[http://dx.doi.org/10.1039/D0QO01247E]
[http://dx.doi.org/10.1021/acs.joc.9b03153] [PMID: 32293177]
[http://dx.doi.org/10.1002/9781118695692]
[http://dx.doi.org/10.2174/138527210793358277]
[http://dx.doi.org/10.1016/S0040-4039(01)92822-9]
[http://dx.doi.org/10.1021/jo00227a038]
[http://dx.doi.org/10.1016/S0040-4020(01)80761-4]
[http://dx.doi.org/10.1021/ol0341039] [PMID: 12633106]
[http://dx.doi.org/10.1055/s-1997-1039]
[http://dx.doi.org/10.1021/ol4016699] [PMID: 23822877]
[http://dx.doi.org/10.1016/S0040-4020(01)90535-6]
[http://dx.doi.org/10.1021/jo00355a029]
[http://dx.doi.org/10.1039/C6CC08731K] [PMID: 27918016]
[http://dx.doi.org/10.1016/S0040-4039(01)00077-6]
[http://dx.doi.org/10.1055/s-1995-3926]
[http://dx.doi.org/10.1021/ol048114t] [PMID: 15496116]
[http://dx.doi.org/10.1021/acs.orglett.1c03575] [PMID: 34851130]
[http://dx.doi.org/10.1016/S0040-4039(00)61432-6]
[http://dx.doi.org/10.1016/S0040-4020(01)80760-2]
[http://dx.doi.org/10.1021/acs.orglett.7b02244] [PMID: 28901154]
[http://dx.doi.org/10.1002/anie.200901484] [PMID: 19444850]
[http://dx.doi.org/10.1055/s-1990-26835]
[http://dx.doi.org/10.1021/jo01301a032]
[http://dx.doi.org/10.1021/jo00080a031]
[http://dx.doi.org/10.1016/S0040-4039(98)02337-5]
[http://dx.doi.org/10.1021/ja3030824] [PMID: 22612535]
[http://dx.doi.org/10.1246/bcsj.59.927]
[http://dx.doi.org/10.1021/ol000031z] [PMID: 10804566]
[http://dx.doi.org/10.1002/anie.202113820] [PMID: 34783149]
[http://dx.doi.org/10.1021/acs.orglett.1c00466] [PMID: 33886335]
[http://dx.doi.org/10.1016/S0040-4039(98)00065-3]
[http://dx.doi.org/10.1007/s10562-020-03390-x]
[http://dx.doi.org/10.1016/S0040-4039(00)92695-9]
[http://dx.doi.org/10.1002/anie.200802482] [PMID: 18702071]
[http://dx.doi.org/10.1016/S0040-4039(03)00317-4]
[http://dx.doi.org/10.1055/s-2003-38079]
[http://dx.doi.org/10.1021/acs.orglett.1c01043] [PMID: 33861616]
[http://dx.doi.org/10.1021/acs.orglett.0c03611] [PMID: 33290655]
[http://dx.doi.org/10.1021/acs.joc.8b02165] [PMID: 30351050]
[http://dx.doi.org/10.1002/1521-3773(20000717)39:14<2501:AID-ANIE2501>3.0.CO;2-T] [PMID: 10941117]
[http://dx.doi.org/10.1021/ol016525t] [PMID: 11720546]
[http://dx.doi.org/10.1021/ol501394k] [PMID: 24922082]
[http://dx.doi.org/10.1021/ol801985q] [PMID: 18826321]
[http://dx.doi.org/10.1021/ol901875z] [PMID: 19764711]
[http://dx.doi.org/10.1021/acscatal.9b04864]
[http://dx.doi.org/10.1021/acs.joc.0c01365] [PMID: 32786647]
[http://dx.doi.org/10.1021/acs.orglett.0c00877] [PMID: 32267157]
[http://dx.doi.org/10.1039/D0SC05409G] [PMID: 34164090]
[http://dx.doi.org/10.1039/D1SC03569J] [PMID: 34745545]
[http://dx.doi.org/10.1021/jm0602763] [PMID: 16913719]
[http://dx.doi.org/10.1039/b509528j] [PMID: 17268614]
[http://dx.doi.org/10.1021/jo010579z] [PMID: 11777443]
[http://dx.doi.org/10.1021/ol702153x] [PMID: 18081300]
[http://dx.doi.org/10.1021/jo026016k] [PMID: 12353998]
[http://dx.doi.org/10.1021/acs.orglett.1c02416] [PMID: 34379418]
[http://dx.doi.org/10.1021/jo0105540] [PMID: 11722203]
[http://dx.doi.org/10.1039/C5OB00329F] [PMID: 25797479]
[http://dx.doi.org/10.1016/S0040-4039(99)02254-6]
[http://dx.doi.org/10.1016/j.tet.2015.12.060]
[http://dx.doi.org/10.1016/S0040-4039(00)97272-1]
[http://dx.doi.org/10.1002/slct.202003413] [PMID: 33363255]
[http://dx.doi.org/10.1021/jo401707j] [PMID: 24060188]
[http://dx.doi.org/10.1002/ajoc.202000356]
[http://dx.doi.org/10.1002/jlac.1995199507156]
[http://dx.doi.org/10.1039/D0RA01043J]
[http://dx.doi.org/10.1039/D0QO01179G]
[http://dx.doi.org/10.3390/md15090276] [PMID: 28867803]
[http://dx.doi.org/10.1039/C7RA06425J]
[http://dx.doi.org/10.4172/pharmaceutical-sciences.1000335]
[http://dx.doi.org/10.1016/j.biopha.2016.12.117] [PMID: 28081470]
[http://dx.doi.org/10.1055/s-1994-22996]
[http://dx.doi.org/10.1055/s-1997-1040]
[http://dx.doi.org/10.1021/jo00117a023]
[http://dx.doi.org/10.1021/ol0065569] [PMID: 11073665]
[http://dx.doi.org/10.1021/jo034571w] [PMID: 12895066]
[http://dx.doi.org/10.1016/j.tetlet.2006.05.176]
[http://dx.doi.org/10.1016/S0022-328X(96)06489-3]
[http://dx.doi.org/10.1021/acs.orglett.1c01762] [PMID: 34251821]
[http://dx.doi.org/10.1021/acs.orglett.1c01301] [PMID: 34013729]
[http://dx.doi.org/10.1021/acs.orglett.1c00148] [PMID: 33629865]
[http://dx.doi.org/10.1016/S0040-4020(01)80421-X]
[http://dx.doi.org/10.1039/C8SC02855A] [PMID: 30393523]
[http://dx.doi.org/10.1021/jo991922r] [PMID: 10808454]
[http://dx.doi.org/10.1021/ol203043h] [PMID: 22149009]
[http://dx.doi.org/10.1021/acs.joc.1c02034] [PMID: 34846892]
[http://dx.doi.org/10.1021/acs.orglett.0c01159] [PMID: 32459097]
[http://dx.doi.org/10.1021/ol000087t] [PMID: 10880221]
[http://dx.doi.org/10.1039/b711613f] [PMID: 17989833]
[http://dx.doi.org/10.1021/ja031946m]] [PMID: 15012118];
b) Trend, R.M.; Ramtohul, Y.K.; Stoltz, B.M. Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation. J. Am. Chem. Soc., 2005, 127(50), 17778-17788. PMID: 15012118
[http://dx.doi.org/10.1021/ja055534k]
[http://dx.doi.org/10.1021/acscatal.0c00103]
[http://dx.doi.org/10.1021/jo991692g] [PMID: 10814117]