A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes

Name: Work Video:
Duration: 3 min 30 s
Vsevolod V. Rostovtsev; Luke G. Green; Valery V. Fokin; K. Barry Sharpless
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1507, 1531, 1567, 1608, 1631, 1678], 'water,': [497], 'organic': [498, 939], 'azides': [499, 1264], 'terminal': [501, 1266], 'alkynes': [502], 'are': [503, 794, 914, 1314], 'readily': [504], 'cleanly': [506], 'converted': [507], 'into': [508], '1,4-disubstituted': [509], '1,2,3-triazoles': [510], 'through': [511], 'highly': [513, 937], 'efficient': [514], 'regioselective': [516], 'copper(I)-catalyzed': [517], 'process': [518, 987], '(see': [519], 'scheme': [520], 'an': [522, 1055, 1255], 'example).': [523], 'Supporting': [524, 526, 542], 'Information': [525], 'information': [527, 543, 573], 'is': [531, 547, 562, 1052, 1351, 1380], 'available': [532, 548, 1650], 'on': [533, 549, 922, 1268], 'WWW': [535, 551], 'under': [536, 552], 'http://www.angewandte.org': [537], 'or': [538, 554, 568, 1062, 1475], 'from': [539, 555, 928, 1263, 1459], 'author.': [541, 557], 'http://www.wiley-vch.de/contents/jc_2002/2002/z19191_s.pdf': [553], 'Please': [558], 'note:': [559], 'publisher': [561], 'not': [563, 1329], 'responsible': [564], 'content': [567], 'functionality': [569], 'any': [571], 'supporting': [572], 'supplied': [574], 'authors.': [577], 'Any': [578], 'queries': [579], '(other': [580], 'than': [581], 'missing': [582], 'content)': [583], 'should': [584], 'be': [585, 799, 1332, 1358, 1451], 'directed': [586], 'corresponding': [589, 1400, 1529], 'article.': [593], 'References': [594], '1': [595, 740, 1138, 1149, 1410], '1a': [596], 'R.': [597, 668, 685, 712, 721, 949, 964, 1025, 1128, 1224], '1,3-Dipolar': [600, 736], '(': [603, 620, 677, 695, 741, 1513, 1573], '),': [604, 621, 678, 696, 742, 1514, 1574], 'Wiley,': [605, 743, 1618], 'New': [606, 744, 1619], 'York,': [607, 745, 1620], '1984,': [608, 746], 'pp.': [609, 625, 682, 700, 1518, 1622], '1–176;': [610], '1b': [611], 'A.': [612, 641, 667, 810, 871, 961, 1079, 1082, 1087, 1088, 1100, 1105, 1109, 1117, 1118, 1156, 1165, 1189, 1225, 1501, 1604], 'Padwa': [613], 'Comprehensive': [615, 671, 689, 1568], 'Organic': [616, 907, 1613], 'Synthesis,': [617], 'Vol.': [618, 675, 693, 739, 1511, 1571], '4': [619, 676, 694, 780], 'Pergamon,': [622, 679, 697, 1575], 'Oxford,': [623, 680, 698, 1576], '1991,': [624, 661, 1150], '1069–1109;': [626], '1c': [627], 'asymmetric': [632], '1,3-dipolar': [633], 'cycloaddition': [634, 986], 'reactions,': [635], 'see': [636, 655, 1298, 1491], 'Gothelf,': [639], 'Jorgensen,': [642, 1242], 'Chem.': [643, 705, 716, 727, 820, 848, 864, 877, 895, 900, 1036, 1041, 1134, 1145, 1160, 1198, 1207, 1282, 1320, 1497], 'Rev.': [644], '1998,': [645, 1171, 1245], '98,': [646], '863–909;': [647], '1d': [648], 'synthetic': [653], 'applications,': [654], 'J.': [656, 750, 752, 765, 767, 816, 818, 847, 853, 859, 862, 875, 1065, 1133, 1144, 1153, 1155, 1158, 1175, 1191, 1196, 1211, 1213, 1221, 1227, 1280, 1495, 1564], 'Mulzer,': [657], 'Org.': [658, 863, 876, 1091, 1121, 1159, 1197, 1216, 1281], 'Synth.': [659], 'Highlights': [660], '77–95.': [662], '2': [663, 1389, 1572], '2a': [664], 'W.-Q.': [665], 'Fan,': [666], 'Katritzky': [669], 'Heterocyclic': [672, 690], 'II,': [674, 692], '1996,': [681, 699], '101–126;': [683], '2b': [684], 'Butler': [687], '621–678;': [701], '2c': [702], 'Banert,': [704, 827, 835], 'Ber.': [706, 728], '1989,': [707, 717, 1123, 1199], '122,': [708, 823], '911–918.': [709], '3': [710], '3a': [711], 'Huisgen,': [713, 722], 'Pure': [714], 'Appl.': [715], '61,': [718], '613–628;': [719], '3b': [720], 'Szeimies,': [724], 'Moebius,': [726], '1967,': [729], '100,': [730], '2494–2507;': [731], '3c': [732], 'Lwowski': [734], 'Chemistry,': [738, 1570], 'chap.': [747, 1578], '5;': [748], '3d': [749], 'Bastide,': [751, 766, 1066], 'Hamelin,': [753, 768], 'Texier,': [755, 770], 'Q.': [757, 772], 'Ven,': [758, 773], 'Bull.': [759, 774, 1069], 'Soc.': [760, 775, 821, 1071, 1135, 1146], 'Chim.': [761, 776, 1070], 'Fr.': [762, 777, 1072], '1973,': [763, 778, 1073], '2555–2579;': [764], '2871–2887.': [779], 'Although': [781, 1367], 'applications': [782], 'which': [783, 926, 941, 988, 997, 1643], 'utilize': [784], 'unique': [786], 'reactivity': [787, 982], 'offered': [788], 'azide': [791, 1401], 'group': [792, 1057], 'itself': [793], 'rare,': [795], 'delightful': [796], 'exceptions': [797], 'can': [798, 1357, 1450], 'found': [800], 'following': [802], 'works:': [803], '4a': [804], 'P.': [805, 1024, 1027, 1076, 1097, 1142, 1192, 1238, 1601], 'Desai,': [806], 'Schildknegt,': [808], 'Agrios,': [811], 'C.': [812, 856, 886, 948, 963, 1164, 1273, 1276, 1317], 'Mossman,': [813], 'Milligan,': [815], 'Aube,': [817], 'Am.': [819], '2000,': [822, 865, 952, 1498, 1517], '7226–7232;': [824], '4b': [825], 'Targets': [828], 'Heterocycl.': [829], 'Syst.': [830], '1999,': [831], '3,': [832], '1–32;': [833], 'Liebigs': [836], 'Ann./Recl.': [837], '1997,': [838, 849, 1139, 1621], '2005–2018;': [839], '4c': [840], 'H.': [842, 885, 1131], 'Pearson,': [843], 'W.-K.': [844], 'Fang,': [845], 'Isr.': [846], '37,': [850], '39–46;': [851], '4d': [852], 'Cao,': [854], 'T.': [857, 1115, 1188, 1585, 1606], 'Fyfe,': [858], 'Stoddart,': [861], '65,': [866], '1937–1946;': [867], '4e': [868], 'B.': [869, 892, 1033, 1228, 1300, 1505, 1593], 'Carboni,': [870], 'Benali,': [872], 'Vaultier,': [874], '1993,': [878], '58,': [879], '3736–3741,': [880], 'references': [882, 1307], 'therein.': [883], '5': [884], 'Kolb,': [887], 'Finn,': [890, 1031], 'Sharpless,': [893, 1034, 1594], 'Angew.': [894, 899, 1035, 1040], '2001,': [896, 903, 1182], '113,': [897], '1198–1220;': [898], 'Int.': [901, 1042], 'Ed.': [902, 1043], '40,': [904], '2004–2021.': [905], '6': [906], 'azides,': [908], 'particularly': [909], 'aliphatic': [912], 'series,': [913], 'exceptionally': [915], 'stable': [916], 'toward': [917], 'common': [919], 'reactive': [920], 'chemicals': [921], "Earth's": [924], 'surface,': [925], 'range': [927], 'dioxygen': [929], 'water': [931], 'aqueous': [934], 'solutions': [935], 'functionalized': [938], 'molecules': [940], 'make': [942], 'up': [943], 'living': [944], 'cells:': [945], 'E.': [946, 958, 1084, 1102, 1111], 'Saxon,': [947, 959], 'Bertozzi,': [950, 965], '287,': [953], '2007–2010;': [954], 'Kiick,': [957], 'D.': [960, 1126, 1152, 1167, 1179], 'Tirrel,': [962], 'Proc.': [966], 'Natl.': [967], 'Acad.': [968], 'Sci.': [969], 'USA': [970], '2002,': [971, 1037, 1044, 1218, 1283], '99,': [972], '19–24.': [973], '7': [974], 'In': [975], 'fact,': [976], 'it': [977], 'was': [978, 1252, 1271, 1392, 1432, 1538, 1548], 'razor': [980], 'sharp': [981], 'window': [983], 'spawned': [989], '“in': [991], 'situ': [992], 'click': [993], 'chemistry”': [994], 'ideas—an': [995], 'approach': [996], 'recently': [998], 'resulted': [999], 'discovery': [1002], 'most': [1005], 'potent': [1006], 'noncovalent': [1007], 'inhibitor': [1008], 'acetylcholinesterase': [1010], 'known': [1011], 'date:': [1013], 'Lewis,': [1016], 'Green,': [1019], 'Z.': [1022], 'Radic,': [1023], 'Carlier,': [1026], 'Taylor,': [1028], '114,': [1038], '1095–1099;': [1039], '1053–1057.': [1046], '8': [1047], 'Unless': [1048], 'acetylene': [1050, 1403], 'component': [1051], 'attached': [1053], 'electron-withdrawing': [1056], 'such': [1058], 'as': [1059, 1344, 1346, 1348, 1360], 'carbonyl': [1061], 'perfluoroalkyl': [1063], 'group:': [1064], 'O.': [1067], 'Henri-Rousseau,': [1068], '2294–2296;': [1074], 'Stepanova,': [1077, 1098], 'Orlova,': [1080], 'Galishev,': [1083, 1101], 'S.': [1085, 1103, 1174, 1492], 'Turbanova,': [1086, 1104], 'Petrov,': [1089, 1119], 'Zh.': [1090, 1120], 'Khim.': [1092, 1122], '1985,': [1093], '21,': [1094], '979–983;': [1095], 'Maleev,': [1107], 'Potekhin,': [1110], 'Kurkutova,': [1113], 'Yu.': [1114], 'Struchkov,': [1116], '25,': [1124], '1613–1618;': [1125], 'Clarke,': [1127], 'Mares,': [1130], 'McNab,': [1132], 'Perkin': [1136, 1147], 'Trans.': [1137, 1148], '1799–1804.': [1140], '9': [1141], 'Zanirato,': [1143], '2789–2796;': [1151], 'Hlasta,': [1154], 'Ackerman': [1157], '1994,': [1161], '59,': [1162], '6184–6189;': [1163], 'Booth,': [1166], 'Philp,': [1168, 1180], 'Tetrahedron': [1169, 1181, 1232], 'Lett.': [1170, 1217, 1233], '39,': [1172], '6987–6990;': [1173], 'Howell,': [1176], 'Spencer,': [1178], '57,': [1183], '4945–4954;': [1184], 'Mock,': [1187, 1204], 'Irra,': [1190], 'Wepsiec,': [1193], 'Adhya,': [1195], '54,': [1200], '5302–5308;': [1201], 'Top.': [1205], 'Curr.': [1206], '1995,': [1208, 1234], '175,': [1209], '1–24;': [1210], 'Chen,': [1212], 'Rebek,': [1214], 'Jr.,': [1215], '4,': [1219], '327–329;': [1220], 'Wijnen,': [1223], 'Steiner,': [1226], 'Engberts,': [1231], '36,': [1235], '5389–5392;': [1236], 'Repasky,': [1239], 'Faraday': [1243], 'Discuss.': [1244], '110,': [1246], '379–389.': [1247], '10': [1248], 'While': [1249], 'manuscript': [1251], 'preparation,': [1254], 'independent': [1256], 'account': [1257], 'copper-catalyzed': [1259], 'synthesis': [1260], '1,4-triazoles': [1262], 'acetylenes': [1267], 'solid': [1269], 'support': [1270], 'reported:': [1272], 'Tornøe,': [1275], 'Christensen,': [1277], 'Meldal,': [1279], '67,': [1284], '3057.': [1285], '11': [1286], 'For': [1287, 1383, 1479, 1521], 'reactions': [1291, 1369, 1485], 'L-ascorbic': [1293], 'acid': [1294, 1313], 'transition': [1296], 'metals,': [1297], 'Davies,': [1301], 'Polyhedron': [1302], '1992,': [1303], '11,': [1304], '285–321,': [1305], 'therein;': [1308], 'redox': [1309], 'properties': [1310], 'ascorbic': [1312], 'summarized': [1315], 'Creutz,': [1318], 'Inorg.': [1319, 1496], '1981,': [1321], '20,': [1322], '4449.': [1323], '12': [1324], 'starting': [1326], 'materials': [1327], 'do': [1328], 'need': [1330], 'dissolved': [1333], 'reaction': [1336, 1339, 1626], 'solvent.': [1337], 'seems': [1340], 'proceed': [1342, 1374], 'just': [1343], 'efficiently': [1345], 'long': [1347], 'adequate': [1349], 'maintained.': [1352], '13': [1353], 'Amazingly,': [1354], 'even': [1355, 1630], 'Cu0': [1356], 'used': [1359], 'source': [1362], 'catalytic': [1365], 'species.': [1366], 'these': [1368], 'may': [1370], 'take': [1371], 'longer': [1372], 'completion,': [1376], 'experimental': [1378], 'procedure': [1379, 1537], 'exceedingly': [1381], 'simple.': [1382], 'example,': [1384, 1522], 'bis-triazole': [1385], 'shown': [1386], 'entry': [1388], '(Table': [1390], '1)': [1391], 'obtained': [1393, 1452, 1549], 'quantitative': [1395], 'yield': [1396, 1534], 'after': [1397], 'components': [1404], '24': [1406], 'h': [1407], 'about': [1409], 'g': [1411], 'coiled': [1413], 'copper': [1414, 1647], 'metal': [1415], 'turnings.': [1416], 'turnings': [1418], 'were': [1419], 'removed': [1420], 'at': [1421], 'end': [1423], 'reaction,': [1426], 'pure': [1429], 'white': [1430], 'product': [1431, 1547], 'collected': [1433], 'simple': [1435], 'filtration.': [1436], 'CCDC': [1438], '186236': [1439], 'contains': [1440], 'supplementary': [1442], 'crystallographic': [1443], 'data': [1444, 1449], 'paper.': [1447], 'These': [1448], 'free': [1453], 'charge': [1455], 'via': [1456], 'www.ccdc.cam.ac.uk/conts/retrieving.html': [1457], '(or': [1458], 'Cambridge': [1461, 1468], 'Crystallographic': [1462], 'Data': [1463], 'Centre,': [1464], '12,': [1465], 'Union': [1466], 'Road,': [1467], 'CB2': [1469], '1EZ,': [1470], 'UK;': [1471], 'fax:': [1472], '(+44)': [1473], '1223-336-033;': [1474], 'protected]).': [1477], 'recent': [1481], 'summary': [1482], 'copper(I)': [1487], 'complexes': [1488], 'dioxygen,': [1490], 'Schindler,': [1493], 'Eur.': [1494], '2311–2326': [1499], 'Blackman,': [1503], 'Tolman': [1506], 'Structure': [1508], 'Bonding,': [1510], '97': [1512], 'Springer,': [1515], 'Berlin,': [1516], '179–211.': [1519], '16': [1520], 'ethyl': [1523], 'propiolate': [1524], 'benzylazide': [1526], 'furnished': [1527], '1,4-triazole': [1530], '55': [1532], '%': [1533], 'when': [1535], 'used,': [1539], 'but': [1540], 'only': [1541], 'trace': [1543], 'amount': [1544], 'one': [1551], 'equivalent': [1552], 'triethylamine': [1554], 'without': [1556], 'exclusion': [1557], 'oxygen.': [1559], '17': [1560], 'van': [1562], 'Koten,': [1563], 'Noltes': [1566], 'Organometallic': [1569], '1982,': [1577], '14,': [1579], '720.': [1581], '18': [1582], 'Lovell,': [1586], 'Rostovtsev,': [1588], 'Fokin,': [1591], 'unpublished': [1597], 'results.': [1598], '19': [1599], 'Doyle,': [1602], 'McKervey,': [1605], 'Ye': [1607], 'Modern': [1609], 'Catalytic': [1610], 'Methods': [1611], 'Synthesis': [1614], 'Diazo': [1616], 'Compounds,': [1617], '163–248.': [1623], '20': [1624], 'proceeded': [1627], 'equally': [1628], 'well': [1629], 'human': [1632], 'plasma': [1633, 1659], '(protein': [1634], 'loading': [1635], '65–85': [1636], 'mg': [1637], 'mL−1,': [1638], 'Cazide=Calkyne=5': [1639], 'mM;': [1640], 'C=100': [1641], 'μM),': [1642], 'indicates': [1644], 'that': [1645], 'species': [1648], 'remained': [1649], 'catalysis': [1653], 'despite': [1654], 'being': [1655], 'heavily': [1656], 'bound': [1657], 'proteins.': [1660], 'Citing': [1661], 'Literature': [1662], 'Volume41,': [1663], 'Issue14July': [1664], '15,': [1665], '2002Pages': [1666], 'This': [1668], 'appears': [1671], 'in:In': [1672], 'Celebration': [1673], 'SharplessNobel': [1676], 'Prize': [1677], '2022:': [1680], 'Click': [1681], 'Bioorthogonal': [1684], 'ReferencesRelatedInformation': [1686]}, 'cited_by_api_url': 'https://api.openalex.org/works?filter=cites:W2145662716', 'counts_by_year': [{'year': 2024, 'cited_by_count': 369}, {'year': 2023, 'cited_by_count': 464}, {'year': 2022, 'cited_by_count': 414}, {'year': 2021, 'cited_by_count': 519}, {'year': 2020, 'cited_by_count': 577}, {'year': 2019, 'cited_by_count': 560}, {'year': 2018, 'cited_by_count': 510}, {'year': 2017, 'cited_by_count': 595}, {'year': 2016, 'cited_by_count': 711}, {'year': 2015, 'cited_by_count': 694}, {'year': 2014, 'cited_by_count': 758}, {'year': 2013, 'cited_by_count': 773}, {'year': 2012, 'cited_by_count': 731}], 'updated_date': '2024-12-17T12:33:19.891634', 'created_date': '2016-06-24'}
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