Abstract
Propargylamines are an important constituent of diverse, biologically active and industrially valuable compounds. These useful, convenient and effective compounds can be synthesized via the A3-coupling reactions between an aldehyde, amine, and alkyne in the presence of a catalyst. In the past years, most of the catalysts containing transition metals were applied in these reactions, but today, various heterogeneous catalysts, especially nanocatalysts are used. The purpose of this review was to introduce some modern catalysts for the A3-coupling reaction.
Keywords: A3-coupling reaction, aldehyde, amine, alkyne, catalyst, transition metal, nanocatalyst.
Graphical Abstract
[http://dx.doi.org/10.1021/jo01039a028]
[http://dx.doi.org/10.1021/jo01037a042]
[http://dx.doi.org/10.1021/jo01031a518]
[http://dx.doi.org/10.1126/science.6332378] [PMID: 6332378]
[http://dx.doi.org/10.1111/j.1471-4159.1989.tb07373.x] [PMID: 2568405]
[http://dx.doi.org/10.1177/0091270005277935] [PMID: 16027398]
[http://dx.doi.org/10.1016/S0047-6374(01)00391-8] [PMID: 12044957]
[http://dx.doi.org/10.1002/14651858.CD000442] [PMID: 12535396]
[http://dx.doi.org/10.1056/NEJM199704243361704] [PMID: 9110909]
[PMID: 1907964]
[http://dx.doi.org/10.1186/s13024-015-0067-y] [PMID: 26758813]
[http://dx.doi.org/10.1007/s40263-014-0206-y] [PMID: 25322951]
[http://dx.doi.org/10.1007/s00702-012-0948-y] [PMID: 23238976]
[http://dx.doi.org/10.1002/med.20248] [PMID: 21793014]
[http://dx.doi.org/10.1007/s00702-015-1395-3] [PMID: 25859841]
[http://dx.doi.org/10.1007/s12640-009-9128-8] [PMID: 19894083]
[http://dx.doi.org/10.1039/c2cs15356d] [PMID: 22422343]
[http://dx.doi.org/10.1002/9783527678174]
[http://dx.doi.org/10.1021/cr100233r] [PMID: 22435608]
[http://dx.doi.org/10.1002/1521-3773(20000915)39:18<3168:AID-ANIE3168>3.0.CO;2-U] [PMID: 11028061]
[http://dx.doi.org/10.1039/C6GC00157B]
[http://dx.doi.org/10.1021/ol100931q] [PMID: 20481612]
[http://dx.doi.org/10.1021/acs.orglett.8b03388] [PMID: 30565459]
[http://dx.doi.org/10.1080/10426500701839825]
[http://dx.doi.org/10.1080/10426507.2015.1067213]
[http://dx.doi.org/10.1016/j.ejmech.2014.03.049] [PMID: 24681979]
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
[http://dx.doi.org/10.1021/acs.joc.8b02998] [PMID: 30592406]
[http://dx.doi.org/10.1021/acs.joc.8b01874] [PMID: 30354108]
[http://dx.doi.org/10.1021/acs.joc.8b02091] [PMID: 30403140]
[http://dx.doi.org/10.1002/hlca.201000280]
[http://dx.doi.org/10.2174/2211544706666161228143222]
[http://dx.doi.org/10.1002/slct.201600414]
[http://dx.doi.org/10.1016/j.catcom.2007.06.018]
[http://dx.doi.org/10.1016/j.molcata.2012.03.023]
[http://dx.doi.org/10.1007/s11164-015-2163-6]
[http://dx.doi.org/ 10.1007/s12633-019-0087-2]
[http://dx.doi.org/10.1002/aoc.3823]
[http://dx.doi.org/10.1007/s12039-018-1572-7]
[http://dx.doi.org/10.1007/s10971-017-4310-6]
[http://dx.doi.org/10.1007/s12633-018-0034-7]
[http://dx.doi.org/10.1007/s11164-019-03878-1]
[http://dx.doi.org/10.1021/ar800214s] [PMID: 19175315]
[http://dx.doi.org/10.1016/S0160-9327(05)80086-9]
[http://dx.doi.org/10.1021/bm049947+] [PMID: 15244467]
[http://dx.doi.org/10.1021/ar020258p] [PMID: 14674781]
[http://dx.doi.org/10.1016/j.cbpa.2010.03.003] [PMID: 20392661]
[http://dx.doi.org/10.1002/anie.201006515] [PMID: 21710674]
[http://dx.doi.org/10.1016/j.ultsonch.2014.06.017] [PMID: 25060117]
[http://dx.doi.org/10.1080/10426507.2015.1091826]
[http://dx.doi.org/10.1002/hc.20626]
[http://dx.doi.org/10.1021/acs.orglett.6b02180] [PMID: 27617698]
[http://dx.doi.org/10.2174/157017808785982158]
[http://dx.doi.org/10.3906/kim-1501-43]
[http://dx.doi.org/10.1002/chem.200305048] [PMID: 14502613]
[http://dx.doi.org/10.1021/acs.joc.5b01452] [PMID: 26214735]
[http://dx.doi.org/10.1002/anie.200461073] [PMID: 15558675]
[http://dx.doi.org/10.1021/ol026293d] [PMID: 12182587]
[http://dx.doi.org/10.1002/anie.201102088] [PMID: 21626634]
[http://dx.doi.org/10.1039/c3cc00118k] [PMID: 23435368]
[http://dx.doi.org/10.1002/adsc.200900293]
[http://dx.doi.org/10.1039/C9CS00253G] [PMID: 31465045]
[http://dx.doi.org/10.1002/ejoc.201900001]
[http://dx.doi.org/10.3762/bjoc.13.53] [PMID: 28405234]
[http://dx.doi.org/10.1039/c2cc33320a] [PMID: 22842770]
[http://dx.doi.org/10.1039/c3cc38287g] [PMID: 23340772]
[http://dx.doi.org/10.1016/j.molcata.2014.08.007]
[http://dx.doi.org/10.1039/C2RA22390B]
[http://dx.doi.org/10.1002/chem.201000587] [PMID: 20583055]
[http://dx.doi.org/10.1039/C5RA02974K]
[http://dx.doi.org/10.1002/chem.201002043] [PMID: 21284044]
[http://dx.doi.org/10.1039/c1gc15518k]
[http://dx.doi.org/10.1039/C4RA10384J]
[http://dx.doi.org/10.1021/acs.chemrev.7b00343] [PMID: 29166000]
[http://dx.doi.org/10.1021/cr300527g] [PMID: 23786461]
[http://dx.doi.org/10.1021/cr500410y] [PMID: 25531056]
[http://dx.doi.org/10.1021/cr8002505] [PMID: 18698737]
[http://dx.doi.org/10.1039/B416268D] [PMID: 15742063]
[http://dx.doi.org/10.1021/ol049936t] [PMID: 15012085]
[http://dx.doi.org/10.1016/j.tetlet.2004.09.079]
[http://dx.doi.org/10.1038/ncomms4884] [PMID: 24848772]
[http://dx.doi.org/10.1021/ol1008312] [PMID: 20441203]
[http://dx.doi.org/10.1021/jo300562j] [PMID: 22563934]
[http://dx.doi.org/10.1039/C5QO00282F]
[http://dx.doi.org/10.1055/s-0033-1338944]
[http://dx.doi.org/10.1021/ol402517e] [PMID: 24237286]
[http://dx.doi.org/10.1039/C5RA04729C]
[http://dx.doi.org/10.1021/acs.joc.5b02554] [PMID: 26726072]
[http://dx.doi.org/10.1002/ejoc.201600343]
[http://dx.doi.org/10.1016/j.catcom.2017.09.020]
[http://dx.doi.org/10.1016/j.tetlet.2017.09.031]
[http://dx.doi.org/10.1016/j.cclet.2014.10.022]
[http://dx.doi.org/10.1021/acs.inorgchem.6b03084] [PMID: 28394133]
[http://dx.doi.org/10.1002/chem.201403927] [PMID: 25212722]
[http://dx.doi.org/10.1016/j.ica.2017.07.038]
[http://dx.doi.org/10.1002/ejoc.201701033]
[http://dx.doi.org/10.1039/C6RA20767G]
[http://dx.doi.org/10.1021/acs.cgd.7b00898]
[http://dx.doi.org/10.1021/jacs.5b02071] [PMID: 25835280]
[http://dx.doi.org/10.1039/C5GC00079C]
[http://dx.doi.org/10.1021/acscatal.7b03370]
[http://dx.doi.org/10.1055/s-0034-1378206]
[http://dx.doi.org/10.1039/c2jm34198k]
[http://dx.doi.org/10.1016/j.carbon.2012.05.002]
[http://dx.doi.org/10.1016/j.cclet.2015.05.021]
[http://dx.doi.org/10.1016/j.tetlet.2016.08.066]
[http://dx.doi.org/10.2298/JSC161221081S]
[http://dx.doi.org/10.1016/j.tet.2013.06.098]
[http://dx.doi.org/10.1021/ol0528641] [PMID: 16597102]
[http://dx.doi.org/10.1016/j.jorganchem.2008.12.008]
[http://dx.doi.org/10.1055/s-2005-872677]
[http://dx.doi.org/10.1039/c2gc35284b]
[http://dx.doi.org/10.1021/ol035781y] [PMID: 14602028]
[http://dx.doi.org/10.1016/j.tet.2007.11.043]
[http://dx.doi.org/10.1021/sc400450t]
[http://dx.doi.org/10.1021/ol051575+] [PMID: 16178542]
[http://dx.doi.org/10.1016/j.tetlet.2013.10.141]
[http://dx.doi.org/10.1016/j.jorganchem.2017.06.019]
[http://dx.doi.org/10.1016/j.cclet.2018.05.036]
[http://dx.doi.org/10.1021/jo500981r] [PMID: 25051223]
[http://dx.doi.org/10.1039/c2dt31609a] [PMID: 22940886]
[http://dx.doi.org/10.1021/acs.cgd.8b00960]
[http://dx.doi.org/10.1021/acs.cgd.8b00833]
[http://dx.doi.org/10.1002/ejoc.201700985]
[http://dx.doi.org/10.1021/acssuschemeng.7b00103]
[http://dx.doi.org/10.1002/anie.201001699] [PMID: 20645367]
[http://dx.doi.org/10.1039/b702287e]
[http://dx.doi.org/10.1002/chem.201201837] [PMID: 22996294]
[http://dx.doi.org/10.1039/b920000b]
[http://dx.doi.org/10.1002/anie.200905684] [PMID: 20419718]
[http://dx.doi.org/10.1080/17518253.2014.939721]
[http://dx.doi.org/10.1007/s00706-017-1948-2]
[http://dx.doi.org/10.1039/C7DT00058H] [PMID: 28350409]
[http://dx.doi.org/10.1039/c0cs00108b] [PMID: 21566801]
[http://dx.doi.org/10.1039/c2nr11558a] [PMID: 22218753]
[http://dx.doi.org/10.3762/bjoc.9.155] [PMID: 23946833]
[http://dx.doi.org/10.1002/ejic.201800085]
[http://dx.doi.org/10.1016/j.tetlet.2007.07.196]
[http://dx.doi.org/10.1039/c3ra46513f]
[http://dx.doi.org/10.1021/ja211092q] [PMID: 22283631]
[http://dx.doi.org/10.1002/hc.21103]
[http://dx.doi.org/10.1246/cl.140426]
[http://dx.doi.org/10.1007/s10562-018-2449-6]
[http://dx.doi.org/10.1055/s-0035-1562114]
[http://dx.doi.org/10.1007/s11030-019-09977-w] [PMID: 31359369]
[http://dx.doi.org/10.1039/b404430d] [PMID: 15263956]
[http://dx.doi.org/10.1021/ol017022q] [PMID: 11784207]
[http://dx.doi.org/10.1021/jo701643h] [PMID: 17999525]
[http://dx.doi.org/10.1021/ol0525260] [PMID: 16381569]
[http://dx.doi.org/10.1016/j.tetlet.2012.08.136]
[http://dx.doi.org/10.1016/j.catcom.2011.09.012]
[http://dx.doi.org/10.1039/C5CC03296B] [PMID: 25993531]
[http://dx.doi.org/10.1002/chem.201502993]] [PMID: 26490447]
[http://dx.doi.org/10.1016/j.tet.2005.07.059]
[http://dx.doi.org/10.1021/jo900507v] [PMID: 19422248]
[http://dx.doi.org/10.1016/j.tetlet.2009.03.014]
[http://dx.doi.org/10.1016/j.tetlet.2009.03.206]
[http://dx.doi.org/10.1021/ol035138b] [PMID: 12943405]
[http://dx.doi.org/10.1002/anie.200352081] [PMID: 14502747]
[http://dx.doi.org/10.1016/j.tetlet.2011.06.067]
[http://dx.doi.org/10.1016/j.molcata.2015.01.021]
[http://dx.doi.org/10.1002/chem.200802643] [PMID: 19177481]
[http://dx.doi.org/10.1039/c2cc17616e] [PMID: 22234426]
[http://dx.doi.org/10.1016/j.tetlet.2009.03.182]
[http://dx.doi.org/10.1002/ejoc.200901084]
[http://dx.doi.org/10.1002/aoc.3071]
[http://dx.doi.org/10.1039/C5CC05752C] [PMID: 26399895]
[http://dx.doi.org/10.1016/j.poly.2016.09.005]