453:
348:
421:
409:
441:
393:
214:
272:
173:
1426:
1277:
1345:
1182:
382:
Palladium compounds owe their reactivity to the ease of interconversion between Pd(0) and palladium(II) intermediates. There is no conclusive evidence however for the involvement of Pd(II) to Pd(IV) conversions in palladium mediated organometallic reactions. One reaction invoking such mechanism was
298:
Various organic groups can bound to palladium and form stable sigma-bonded complexes. The stability of the bonds in terms of bond dissociation energy follows the trend: Pd-Alkynyl > Pd-Vinyl â Pd-Aryl > Pd-Alkyl and the metal-carbon bond length changes in the opposite direction: Pd-Alkynyl
221:
Palladium(II) acetate and related compounds are common reagents because the carboxylates are good leaving groups with basic properties. For example palladium trifluoroacetate has been demonstrated to be effective in aromatic
649:
Peter K. Byers; Allan J. Canty; Brian W. Skelton; Allan H. White (1986). "The oxidative addition of lodomethane to and the X-ray structure of the organopalladium(IV) product fac-(bpy = 2,2-bipyridyl)".
675:
Antonio J. Mota & Alain Dedieu (2007). "Through-Space
Intramolecular Palladium Rearrangement in Substituted Aryl Complexes: Theoretical Study of the Aryl to Alkylpalladium Migration Process".
513:
Joshua S. Dickstein; Carol A. Mulrooney; Erin M. O'Brien; Barbara J. Morgan & Marisa C. Kozlowski (2007). "Development of a
Catalytic Aromatic Decarboxylation Reaction".
860:
206:, ethylene is converted to acetaldehyde via nucleophilic attack of hydroxide on a Pd(II)-ethylene intermediate followed by formation of a vinyl alcohol complex.
199:
177:
315:
311:
452:
347:
335:
408:
420:
853:
147:
577:
Igor
Dubovyk; Iain D. G. Watson & Andrei K. Yudin (2007). "Chasing the Proton Culprit from Palladium-Catalyzed Allylic Amination".
1558:
440:
492:
202:. In this complex, the diene is easily displaced, which makes it a favored precursor to catalysts. In the industrially important
711:
Liansheng Wang; Yi Pan; Xin Jiang; Hongwen Hu (2000). "Palladium catalyzed reaction of α-chloromethylnaphthalene with olefins".
551:"Stereoselective 1,4-Functionalizations of Conjugated Dienes: cis- and trans-1-Acetoxy-4-(Dicarbomethoxymethyl)-2-Cyclohexene"
846:
247:
814:
Pd-Catalyzed Alkyl to Aryl
Migration and Cyclization: An Efficient Synthesis of Fused Polycycles via Multiple C-H Activation
793:
235:
759:
Synthesis of
Substituted Carbazoles by a Vinylic to Aryl Palladium Migration Involving Domino C-H Activation Processes
392:
1415:
1410:
1405:
1400:
1395:
1390:
1385:
1380:
1375:
1370:
1365:
1360:
1350:
1293:
1187:
1108:
1103:
960:
165:
1451:
1153:
1113:
1093:
1081:
1049:
1014:
982:
950:
945:
905:
151:
920:
884:
838:
279:
198:
Unlike Ni(II), but similar to Pt(II), Pd(II) halides form a variety of alkene complexes. The premier example is
1496:
1491:
1486:
1481:
1476:
1471:
1466:
1461:
1456:
1441:
1431:
1282:
1257:
1252:
1237:
1222:
1202:
1197:
1148:
1076:
1059:
1009:
1004:
999:
994:
970:
930:
31:
742:
Gunter Karig, Maria-Teresa Moon, Nopporn
Thasana, and Timothy Gallagher Org. Lett., Vol. 4, No. 18, 2002 3116
1446:
1436:
1247:
1232:
1217:
1207:
1192:
1133:
1118:
1098:
1088:
1069:
1064:
1054:
1044:
987:
955:
925:
915:
1355:
1270:
1212:
1175:
1170:
1158:
1138:
1128:
1034:
1029:
1024:
965:
940:
83:
271:
217:
Catalytic cycle for the industrially significant Wacker
Process for oxidation of ethylene to acetaldehyde
1163:
975:
910:
900:
447:
and in certain intramolecular couplings synthetic value was demonstrated regardless of oxidation state:
283:
1242:
1227:
1039:
1019:
432:
339:
259:
158:
1143:
713:
465:
613:
323:
368:
818:
789:
785:
693:
595:
579:
555:
531:
488:
331:
287:
213:
207:
140:
101:
86:
55:
826:
769:
743:
722:
685:
657:
633:
587:
523:
621:
617:
223:
59:
38:
compounds and their reactions. Palladium is often used as a catalyst in the reduction of
620:(is reported to absorb the amine protons that would otherwise trigger isomerization) in
330:
Pd-C bonds. This chemistry forms the basis of a large class of organic reactions called
17:
203:
132:
1957 - Tetrakis(triphenylphosphine)palladium(0) is reported by
Malatesta and Angoletta.
108:
726:
1552:
1515:
677:
652:
384:
372:
327:
243:
136:
72:
51:
740:
C-H Activation and
Palladium Migration within Biaryls under Heck Reaction Conditions
801:
415:
In related work the intermediate associated with the hydride shift remains Pd(II):
400:
387:. This reaction was accompanied by a 1,5-hydrogen shift in the presence of amines:
119:
76:
816:
Qinhua Huang, Alessia Fazio, Guangxiu Dai, Marino A. Campo, and
Richard C. Larock
550:
172:
762:
515:
319:
307:
255:
251:
97:
35:
697:
599:
535:
661:
111:
90:
47:
797:
830:
773:
747:
689:
637:
591:
527:
161:
is a coupling reaction of terminal alkynes with aryl or vinyl halides.
870:
428:
115:
43:
39:
143:
of a halogenide with an olefin. Pd(0) intermediates are implicated.
263:
239:
171:
399:
The hydride shift was envisaged as taking place through a Pd(IV)
842:
254:
3. These intermediates too react with nucleophiles for example
50:. This process involves the formation of a palladium-carbon
485:
Handbook of Organopalladium Chemistry for Organic Synthesis
104:
makes it possible to carry out high pressure hydrogenation.
632:
V. P. Ananikov et al., Organometallics, 2005, 24, 715
371:
ligand) It was synthesized by oxidative addition of
1507:
363:compound was described in 1986. This complex is Me
278:Allylpalladium intermediates also feature in the
435:are postulated between different palladacycles:
54:. Palladium is also prominent in carbon-carbon
854:
8:
503:Phillips, F. C.; Am. Chem. J. 1894, 16, 255.
549:Jan-E. BĂ€ckvall and Jan O. VĂ„gberg (1993).
861:
847:
839:
873:with other elements in the periodic table
427:and in other work (a novel synthesis of
316:tetrakis(triphenylphosphine)palladium(0)
312:tris(dibenzylideneacetone)dipalladium(0)
299:< Pd-Vinyl â Pd-Aryl < Pd-Alkyl.
266:in allylic amination as depicted below
212:
477:
294:Palladium-carbon sigma-bonded complexes
890:
336:palladium-catalyzed coupling reactions
234:The iconic complex in this series is
200:dichloro(1,5âcyclooctadiene)palladium
7:
1532:Academic research, no widespread use
280:Trost asymmetric allylic alkylation
148:Trost asymmetric allylic alkylation
89:to palladium metal by contact with
383:described in 2000 and concerned a
246:react with palladium(II) salts to
66:Organopalladium chemistry timeline
25:
1424:
1343:
1275:
1180:
880:
761:Jian Zhao and Richard C. Larock
451:
439:
419:
407:
391:
346:
270:
168:for C-N bond-forming reactions.
367:Pd(IV)(I)bpy (bpy = bidentate
318:. These complexes react with
210:also bind with palladium(II).
1:
794:bis(diphenylphosphino)methane
727:10.1016/S0040-4039(99)02154-1
487:Ei-Negishi John Wiley (2002)
326:to R-Pd-X intermediates with
236:allylpalladium chloride dimer
82:1894 - Phillips reports that
79:over palladium with hydrogen.
286:and an oxo variation in the
1575:
166:Buchwald-Hartwig amination
1559:Organopalladium compounds
1421:
1340:
892:
888:
878:
164:1994 - The Pd-catalyzed
152:nucleophilic substitution
100:technology introduced by
28:Organopalladium chemistry
565:, vol. 8, p. 5
431:with two Pd migrations)
310:Pd(0) compounds include
242:compounds with suitable
34:that deals with organic
32:organometallic chemistry
18:Organopalladium compound
1527:Many uses in chemistry
1522:Core organic chemistry
303:Palladium(0) compounds
218:
185:
84:palladium(II) chloride
765:, Vol. 7, No. 4, 701
338:). An example is the
284:Carroll rearrangement
216:
175:
75:reports reduction of
58:, as demonstrated in
662:10.1039/C39860001722
340:Sonogashira reaction
182:(1,5-cyclooctadiene)
159:Sonogashira coupling
714:Tetrahedron Letters
586:(46): 14172â14173.
466:Palladium compounds
361:organopalladium(IV)
355:Organopalladium(IV)
614:triethyl phosphite
332:coupling reactions
324:oxidative addition
248:pi-allyl complexes
219:
186:
122:with catalyst PdCl
56:coupling reactions
1546:
1545:
1502:
1501:
831:10.1021/ja047980y
825:, 126, 7460-7461
819:J. Am. Chem. Soc.
790:palladium acetate
786:diphenylacetylene
774:10.1021/ol0474655
748:10.1021/ol026426v
690:10.1021/jo701701s
684:(25): 9669â9678.
656:(23): 1722â1724.
638:10.1021/om0490841
592:10.1021/ja076659n
580:J. Am. Chem. Soc.
563:Collected Volumes
556:Organic Syntheses
528:10.1021/ol070749f
522:(13): 2441â2444.
288:Saegusa oxidation
208:Fullerene ligands
141:coupling reaction
102:Vladimir Ipatieff
16:(Redirected from
1566:
1538:
1533:
1528:
1523:
1428:
1427:
1347:
1346:
1279:
1278:
1184:
1183:
881:
863:
856:
849:
840:
833:
811:
805:
782:
776:
756:
750:
737:
731:
730:
708:
702:
701:
672:
666:
665:
646:
640:
630:
624:
610:
604:
603:
574:
568:
566:
559:
546:
540:
539:
510:
504:
501:
495:
482:
455:
443:
423:
411:
395:
350:
274:
194:Alkene complexes
60:tandem reactions
21:
1574:
1573:
1569:
1568:
1567:
1565:
1564:
1563:
1549:
1548:
1547:
1542:
1541:
1536:
1531:
1526:
1521:
1503:
1425:
1344:
1276:
1181:
874:
867:
837:
836:
812:
808:
796:(dppm) and the
783:
779:
757:
753:
738:
734:
710:
709:
705:
674:
673:
669:
648:
647:
643:
631:
627:
611:
607:
576:
575:
571:
561:
548:
547:
543:
512:
511:
507:
502:
498:
483:
479:
474:
462:
378:
369:2,2'-bipyridine
366:
357:
305:
296:
260:malonate esters
232:
230:Allyl complexes
224:decarboxylation
196:
191:
181:
129:
125:
68:
30:is a branch of
23:
22:
15:
12:
11:
5:
1572:
1570:
1562:
1561:
1551:
1550:
1544:
1543:
1540:
1539:
1534:
1529:
1524:
1519:
1516:Chemical bonds
1512:
1511:
1509:
1505:
1504:
1500:
1499:
1494:
1489:
1484:
1479:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1439:
1434:
1429:
1422:
1419:
1418:
1413:
1408:
1403:
1398:
1393:
1388:
1383:
1378:
1373:
1368:
1363:
1358:
1353:
1348:
1341:
1338:
1337:
1333:
1332:
1329:
1326:
1323:
1320:
1317:
1314:
1311:
1308:
1305:
1302:
1299:
1296:
1291:
1288:
1285:
1280:
1273:
1268:
1264:
1263:
1260:
1255:
1250:
1245:
1240:
1235:
1230:
1225:
1220:
1215:
1210:
1205:
1200:
1195:
1190:
1185:
1178:
1173:
1167:
1166:
1161:
1156:
1151:
1146:
1141:
1136:
1131:
1126:
1121:
1116:
1111:
1106:
1101:
1096:
1091:
1086:
1084:
1079:
1073:
1072:
1067:
1062:
1057:
1052:
1047:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1007:
1002:
997:
992:
990:
985:
979:
978:
973:
968:
963:
958:
953:
948:
943:
937:
936:
933:
928:
923:
918:
913:
908:
903:
897:
896:
893:
891:
889:
887:
879:
876:
875:
868:
866:
865:
858:
851:
843:
835:
834:
806:
777:
751:
732:
721:(5): 725â727.
703:
667:
641:
625:
605:
569:
541:
505:
496:
476:
475:
473:
470:
469:
468:
461:
458:
457:
456:
445:
444:
425:
424:
413:
412:
397:
396:
376:
364:
356:
353:
352:
351:
304:
301:
295:
292:
276:
275:
244:leaving groups
231:
228:
204:Wacker process
195:
192:
190:
187:
179:
170:
169:
162:
155:
144:
133:
130:
127:
123:
109:Wacker process
107:1956 - In the
105:
94:
80:
67:
64:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1571:
1560:
1557:
1556:
1554:
1535:
1530:
1525:
1520:
1517:
1514:
1513:
1510:
1506:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1423:
1420:
1417:
1414:
1412:
1409:
1407:
1404:
1402:
1399:
1397:
1394:
1392:
1389:
1387:
1384:
1382:
1379:
1377:
1374:
1372:
1369:
1367:
1364:
1362:
1359:
1357:
1354:
1352:
1349:
1342:
1339:
1335:
1334:
1330:
1327:
1324:
1321:
1318:
1315:
1312:
1309:
1306:
1303:
1300:
1297:
1295:
1292:
1289:
1286:
1284:
1281:
1274:
1272:
1269:
1266:
1265:
1261:
1259:
1256:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1221:
1219:
1216:
1214:
1211:
1209:
1206:
1204:
1201:
1199:
1196:
1194:
1191:
1189:
1186:
1179:
1177:
1174:
1172:
1169:
1168:
1165:
1162:
1160:
1157:
1155:
1152:
1150:
1147:
1145:
1142:
1140:
1137:
1135:
1132:
1130:
1127:
1125:
1122:
1120:
1117:
1115:
1112:
1110:
1107:
1105:
1102:
1100:
1097:
1095:
1092:
1090:
1087:
1085:
1083:
1080:
1078:
1075:
1074:
1071:
1068:
1066:
1063:
1061:
1058:
1056:
1053:
1051:
1048:
1046:
1043:
1041:
1038:
1036:
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1013:
1011:
1008:
1006:
1003:
1001:
998:
996:
993:
991:
989:
986:
984:
981:
980:
977:
974:
972:
969:
967:
964:
962:
959:
957:
954:
952:
949:
947:
944:
942:
939:
938:
934:
932:
929:
927:
924:
922:
919:
917:
914:
912:
909:
907:
904:
902:
899:
898:
894:
886:
883:
882:
877:
872:
869:Compounds of
864:
859:
857:
852:
850:
845:
844:
841:
832:
828:
824:
821:
820:
815:
810:
807:
803:
799:
795:
791:
787:
781:
778:
775:
771:
768:
764:
760:
755:
752:
749:
745:
741:
736:
733:
728:
724:
720:
716:
715:
707:
704:
699:
695:
691:
687:
683:
680:
679:
678:J. Org. Chem.
671:
668:
663:
659:
655:
654:
653:Chem. Commun.
645:
642:
639:
635:
629:
626:
623:
619:
615:
609:
606:
601:
597:
593:
589:
585:
582:
581:
573:
570:
564:
558:
557:
552:
545:
542:
537:
533:
529:
525:
521:
518:
517:
509:
506:
500:
497:
494:
493:0-471-31506-0
490:
486:
481:
478:
471:
467:
464:
463:
459:
454:
450:
449:
448:
442:
438:
437:
436:
434:
430:
422:
418:
417:
416:
410:
406:
405:
404:
402:
394:
390:
389:
388:
386:
385:Heck reaction
380:
374:
373:methyl iodide
370:
362:
354:
349:
345:
344:
343:
341:
337:
333:
329:
325:
321:
317:
313:
309:
302:
300:
293:
291:
289:
285:
281:
273:
269:
268:
267:
265:
261:
258:derived from
257:
253:
249:
245:
241:
237:
229:
227:
225:
215:
211:
209:
205:
201:
193:
189:Palladium(II)
188:
183:
174:
167:
163:
160:
156:
153:
149:
145:
142:
138:
137:Heck reaction
134:
131:
121:
117:
113:
110:
106:
103:
99:
95:
92:
88:
85:
81:
78:
74:
73:A. N. Zaitsev
70:
69:
65:
63:
61:
57:
53:
52:covalent bond
49:
45:
41:
37:
33:
29:
19:
1537:Bond unknown
1123:
822:
817:
813:
809:
802:pivalic acid
780:
766:
758:
754:
739:
735:
718:
712:
706:
681:
676:
670:
651:
644:
628:
608:
583:
578:
572:
562:
554:
544:
519:
514:
508:
499:
484:
480:
446:
426:
414:
401:metallacycle
398:
381:
360:
358:
306:
297:
277:
233:
220:
197:
120:acetaldehyde
77:benzophenone
27:
26:
379:Pd(II)bpy.
157:1975 - The
146:1973 - The
135:1972 - The
784:Reagents:
763:Org. Lett.
612:Reagents:
516:Org. Lett.
472:References
433:equilibria
359:The first
320:halocarbon
308:Zerovalent
256:carbanions
176:Sample of
1518:to carbon
252:hapticity
118:react to
98:Autoclave
36:palladium
1553:Category
800:salt of
698:18001098
616:ligand,
600:17960935
536:17542594
460:See also
328:covalent
282:and the
262:or with
238:(APC).
112:ethylene
91:ethylene
48:hydrogen
1336:
804:(CsPiv)
798:caesium
429:indoles
322:R-X in
250:having
96:1907 -
87:reduces
71:1873 -
44:alkynes
40:alkenes
1508:Legend
871:carbon
696:
598:
534:
491:
264:amines
116:oxygen
375:to Me
334:(see
240:Allyl
150:is a
139:is a
126:/CuCl
46:with
823:2004
767:2005
694:PMID
596:PMID
532:PMID
489:ISBN
314:and
178:PdCl
114:and
42:and
1482:CEs
1477:CCf
1472:CBk
1467:CCm
1462:CAm
1457:CPu
1452:CNp
1442:CPa
1437:CTh
1416:CYb
1411:CTm
1406:CEr
1401:CHo
1396:CDy
1391:CTb
1386:CGd
1381:CEu
1376:CSm
1371:CPm
1366:CNd
1361:CPr
1356:CCe
1351:CLa
1331:Og
1328:Ts
1325:Lv
1322:Mc
1319:Fl
1316:Nh
1313:Cn
1310:Rg
1307:Ds
1304:Mt
1301:Hs
1298:Bh
1294:CSg
1290:Db
1287:Rf
1271:CRa
1267:Fr
1262:Rn
1258:CAt
1253:CPo
1248:CBi
1243:CPb
1238:CTl
1233:CHg
1228:CAu
1223:CPt
1218:CIr
1213:COs
1208:CRe
1198:CTa
1193:CHf
1188:CLu
1176:CBa
1171:CCs
1164:CXe
1154:CTe
1149:CSb
1144:CSn
1139:CIn
1134:CCd
1129:CAg
1124:CPd
1119:CRh
1114:CRu
1109:CTc
1104:CMo
1099:CNb
1094:CZr
1082:CSr
1077:CRb
1070:CKr
1065:CBr
1060:CSe
1055:CAs
1050:CGe
1045:CGa
1040:CZn
1035:CCu
1030:CNi
1025:CCo
1020:CFe
1015:CMn
1010:CCr
1000:CTi
995:CSc
988:CCa
976:CAr
971:CCl
956:CSi
951:CAl
946:CMg
941:CNa
935:Ne
906:CBe
901:CLi
895:He
827:doi
770:doi
744:doi
723:doi
686:doi
658:doi
634:doi
622:THF
618:DBU
588:doi
584:129
524:doi
1555::
1497:No
1492:Md
1487:Fm
1447:CU
1432:Ac
1283:Lr
1203:CW
1159:CI
1089:CY
1005:CV
983:CK
966:CS
961:CP
931:CF
926:CO
921:CN
916:CC
911:CB
885:CH
792:,
788:,
719:41
717:.
692:.
682:72
594:.
560:;
553:.
530:.
403::
342::
290:.
226::
62:.
862:e
855:t
848:v
829::
772::
746::
729:.
725::
700:.
688::
664:.
660::
636::
602:.
590::
567:.
538:.
526::
520:9
377:2
365:3
184:.
180:2
154:.
128:2
124:2
93:.
20:)
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