20:
719:
393:
1759:
1610:
1678:
1515:
299:
469:
197:), is included in the list of important catalysts. The simple olefin complexes chlorobis(ethylene)rhodium dimer, chlorobis(cyclooctene)rhodium dimer, and cyclooctadiene rhodium chloride dimer are often used as sources of "RhCl", exploiting the lability of the alkene ligands or their susceptibility to removal by hydrogenation. (η-
357:(SET) mechanism is likely to be operative for the C−S bond cleavage. Unlike analogous (phenylazo)phenolato compound the orthometalated thiolato complex exhibits a fully reversible oxidative wave at 0.82 V vs Ag/AgCl and this response is supposed to be primarily centered on the thiolato sulfur atom.
1147:
H.-J.Drexler; Songlin Zhang; Ailing Sun; A. Spannenberg; A. Arrieta; A. Preetz; D. Heller (2004). "Cationic Rh-bisphosphine-diolefin complexes as precatalysts for enantioselective catalysis––what information do single crystal structures contain regarding product chirality?".
84:
of -III to +V, but rhodium(I) and rhodium(III) are the more common. Rhodium(I) compounds (d configuration) usually occur with square planar or trigonal bipyramidal geometries, while rhodium (III) compounds (d configuration) typically have an octahedral geometry.
666:
887:
341:
via in situ C(sp)−H and C(sp)−S bond scissions. This is the first example for a coordination compound of (phenylazo)thiolate ligand. The mechanism of formation of orthometalated
280:
276:. The latter reacts with olefins and with CO to give organometallic complexes, often concomitant with reduction to Rh(I). Cyclopentadienyl complexes of rhodium include the
497:
162:
1193:
740:
491:
often rely on rhodium-based catalysts. Water-soluble catalysts have also been developed. They facilitate the separation of the products from the catalyst.
1049:
Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992). "Eastman
Chemical Company Acetic Anhydride Process".
977:-Assisted C-H and C-S Bond Scissions: Isomeric Self-Association of Organorhodium(III) Thiolato Complex. Synthesis, Structure, and Electrochemistry".
1096:
178:
170:
1186:
174:
1037:
930:
1125:
1891:
166:
80:
Organometallic rhodium compounds share many characteristics with those of iridium, but less so with cobalt. Rhodium can exist in
946:
Bradford B. Wayland; Sujuan Ba; Alan E. Sherry (1991). "Activation of
Methane and Toluene by Rhodium(II) Porphyrin Complexes".
298:
1179:
19:
1032:
Hartwig, J. F. Organotransition Metal
Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010.
106:
94:
291:
Strong donor ligands - hydride, silyl, boryl - are required to stabilize Rh(V). This oxidation state is invoked in
1748:
1743:
1738:
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1723:
1718:
1713:
1708:
1703:
1698:
1693:
1683:
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1436:
1293:
272:
Rhodium is usually supplied commercially in the Rh(III) oxidation state, the main starting reagent being hydrated
1784:
1486:
1456:
1446:
1426:
1414:
1382:
1347:
1315:
1283:
1278:
1238:
182:
1253:
1217:
1171:
60:
Stable organorhodium compounds and transient organorhodium intermediates are used as catalyst such as in olefin
1829:
1824:
1819:
1814:
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1804:
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1774:
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1615:
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704:
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35:
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1397:
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1320:
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240:
is one example, even it exists in equilibrium with a dimeric Rh(I) derivative. Although not organometallic,
186:
1258:
1248:
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1603:
1545:
1508:
1503:
1491:
1471:
1461:
1367:
1362:
1357:
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1273:
321:
chemistry. Although such compounds are well documented in the literature rhodium(III) cyclometalates with
1496:
1308:
1243:
1233:
697:
329:
rhodium(III) thiolato complex trans- was synthesized from benzyl 2-(phenylazo)phenyl thioether and RhCl
1575:
1560:
1372:
1352:
1051:
677:
158:
326:
1476:
708:
693:
661:{\displaystyle {\ce {{\overset {alkene}{RHC=CH2}}+{CO}+H2->{\overset {aldehydes}{RCH2CH2CHO}}}}}
273:
241:
685:
477:
416:
1077:
Cornils, B.; Herrmann, W. A. (eds.) "Aqueous-Phase
Organometallic Catalysis" VCH, Weinheim: 1998
1129:
1092:
1033:
995:
926:
882:{\displaystyle {\ce {{\overset {nitrobenzene}{PhNO2}}+ {C6H6}+ 3CO -> {PhNHCOPh}+ {2CO2}}}}
277:
234:
1157:
1121:
1060:
1017:
987:
955:
488:
424:
397:
374:
253:
198:
81:
69:
61:
54:
345:
derivative was described to proceed via initial coordination of azo-nitrogen followed by
432:
386:
318:
233:
Unlike the prevalence of cobalt(II) complexes, compounds of rhodium(II) are rare. The
1885:
1848:
1064:
712:
681:
428:
420:
382:
346:
118:
65:
46:
979:
731:
322:
311:
718:
325:
function are spare. A typical example of this category viz. novel hexacoordinated
1161:
378:
392:
365:
Despite its high cost, rhodium is heavily relied on as a commercial catalyst.
342:
292:
1021:
973:
K. Pramanik; U. Das; B. Adhikari; D. Chopra; H. Stoeckli-Evans (2008). "RhCl
405:
353:
plays a crucial role in the C(sp)−S cleavage process. Reductive cleavage by
257:
237:
31:
1133:
999:
1126:
10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8
385:
of methanol, although it has largely been supplanted by the iridium-based
1112:
Knowles, William S. (2002). "Asymmetric
Hydrogenations (Nobel Lecture)".
50:
959:
93:
Rhodium(0) complexes are binary carbonyls, the principal examples being
314:
261:
39:
991:
1203:
561:
43:
811:
568:
468:
717:
481:
423:. The related Tennessee Eastman acetic anhydride process affords
409:
391:
297:
18:
1012:
Hosea Cheung, Robin S. Tanke, G. Paul
Torrence "Acetic Acid" in
1175:
734:
reduction is another reaction catalysed by this compound type:
302:
Rh-catalyzed borylation reactions involve Rh(V) intermediates.
1089:
Organotransition metal chemistry- From bonding to
Catalysis
696:(intramolecular hydride transfer or olefin insertion), and
722:
Structure of , a precatalyst for asymmetric hydrogenation.
874:
844:
823:
792:
779:
757:
645:
632:
612:
599:
553:
523:
906:
923:
743:
500:
472:
A rhodium-based hydroformylation catalyst, where PAr
281:
pentamethylcyclopentadienyl rhodium dichloride dimer
49:, and the study of rhodium and rhodium compounds as
1840:
703:Cationic organorhodium(I) catalysts are useful for
133:. In contrast to the stability of the homologous Co
881:
707:, which are applied to bioactive products such as
660:
76:Classification based on principal oxidation states
684:of olefins. The mechanism of catalysis involves
163:bis(triphenylphosphine)rhodium carbonyl chloride
256:via organometallic intermediates. Rhodium(II)
1014:Ullmann's Encyclopedia of Industrial Chemistry
1187:
908:Sanshiro Komiya Ed. S. Komiya, M. Hurano 1997
8:
349:substitution at the pendant phenyl ring. PPh
117:. These compounds are obtained by reductive
317:compounds constitute an important class of
1194:
1180:
1172:
916:
914:
377:is an industrial method for the making of
369:Acetic acid and acetic anhydride syntheses
1206:with other elements in the periodic table
925:(4th ed.). USA: Wiley-Interscience.
873:
868:
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859:
851:
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522:
517:
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502:
501:
499:
185:. Although not formally organometallic,
467:
1114:Angewandte Chemie International Edition
898:
1223:
179:dicarbonyl(acetylacetonato)rhodium(I)
171:cyclooctadiene rhodium chloride dimer
23:Cyclooctadiene rhodium chloride dimer
7:
1865:Academic research, no widespread use
175:chlorobis(cyclooctene)rhodium dimer
157:Rhodium(I) complexes are important
676:Wilkinson's catalyst is used as a
14:
1757:
1676:
1608:
1513:
1213:
167:chlorobis(ethylene)rhodium dimer
337:O in the presence of excess PPh
68:, olefin isomerization and the
834:
828:
602:
586:
580:
574:
400:for production of acetic acid.
1:
1016:, 2002, Wiley-VCH, Weinheim.
1162:10.1016/j.tetasy.2004.06.036
1091:. University Science Books.
1065:10.1016/0920-5861(92)80188-S
921:Crabtree, Robert H. (2005).
692:, π-complexation of alkene,
480:or its sulfonated analogue
396:The catalytic cycle of the
161:. Common complexes include
121:of rhodium(III) salts or Rh
107:hexadecacarbonylhexarhodium
95:tetrarhodium dodecacarbonyl
1908:
1754:
1673:
1225:
1221:
1211:
1087:Hartwig, John F. (2010).
705:asymmetric hydrogenations
183:rhodium carbonyl chloride
1022:10.1002/14356007.a01_045
355:single electron transfer
36:organometallic compounds
1892:Organorhodium compounds
28:Organorhodium chemistry
1860:Many uses in chemistry
1855:Core organic chemistry
1150:Tetrahedron: Asymmetry
883:
723:
662:
617:
485:
408:active species is the
401:
303:
278:half-sandwich compound
24:
884:
721:
709:pharmaceutical agents
698:reductive elimination
663:
557:
471:
395:
301:
260:complexes react with
159:homogeneous catalysts
22:
741:
678:homogeneous catalyst
498:
187:Wilkinson's catalyst
960:10.1021/ja00014a025
876:
848:
846:
825:
794:
781:
759:
694:migratory insertion
647:
634:
616:
614:
601:
567:
555:
525:
415:-. which undergoes
274:rhodium trichloride
242:rhodium(II) acetate
205:are derived from Rh
879:
864:
826:
813:
782:
769:
747:
724:
686:oxidative addition
658:
635:
622:
589:
584:
543:
513:
486:
478:triphenylphosphine
417:oxidative addition
402:
304:
25:
1879:
1878:
1835:
1834:
1120:(12): 1999–2007.
1098:978-1-891389-53-5
992:10.1021/ic7016006
954:(14): 5305–5311.
867:
854:
849:
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785:
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763:
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655:
654:
650:
638:
625:
592:
579:
572:
565:
546:
538:
530:
529:
516:
507:
489:Hydroformylations
361:Main applications
254:cyclopropanations
235:sandwich compound
55:organic reactions
1899:
1871:
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1069:
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1010:
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964:
963:
948:J. Am. Chem. Soc
943:
937:
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918:
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903:
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623:
620:
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583:
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566:
564:hydroformylation
563:
554:
551:
544:
539:
536:
531:
527:
526:
524:
521:
514:
512:
505:
503:
464:Hydroformylation
425:acetic anhydride
398:Monsanto process
375:Monsanto process
149:is very labile.
82:oxidation states
70:Monsanto process
62:hydroformylation
1907:
1906:
1902:
1901:
1900:
1898:
1897:
1896:
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1859:
1854:
1836:
1758:
1677:
1609:
1514:
1207:
1200:
1170:
1169:
1156:(14): 2139–50.
1146:
1145:
1141:
1111:
1110:
1106:
1099:
1086:
1085:
1081:
1076:
1072:
1052:Catalysis Today
1048:
1047:
1043:
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1027:
1011:
1007:
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967:
945:
944:
940:
933:
920:
919:
912:
904:
900:
895:
739:
738:
729:
727:Other reactions
691:
674:
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504:
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78:
17:
12:
11:
5:
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1894:
1884:
1883:
1877:
1876:
1873:
1872:
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1857:
1852:
1849:Chemical bonds
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1209:
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1201:
1199:
1198:
1191:
1184:
1176:
1168:
1167:
1139:
1104:
1097:
1079:
1070:
1041:
1025:
1005:
986:(2): 429–438.
974:
965:
938:
931:
910:
897:
896:
894:
891:
890:
889:
871:
862:
858:
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520:
511:
473:
465:
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452:
448:
444:
440:
433:methyl acetate
387:Cativa process
370:
367:
362:
359:
350:
338:
334:
330:
327:orthometalated
319:organometallic
312:Cyclometalated
308:
305:
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285:
269:
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16:Field of study
15:
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2:
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1379:
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1359:
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1242:
1240:
1237:
1235:
1232:
1231:
1227:
1219:
1216:
1215:
1210:
1205:
1202:Compounds of
1197:
1192:
1190:
1185:
1183:
1178:
1177:
1174:
1163:
1159:
1155:
1151:
1143:
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1123:
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1038:1-891389-53-X
1035:
1029:
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1019:
1015:
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1006:
1001:
997:
993:
989:
985:
982:
981:
969:
966:
961:
957:
953:
949:
942:
939:
934:
932:0-471-66256-9
928:
924:
917:
915:
911:
907:
902:
899:
892:
869:
860:
856:
839:
818:
808:
799:
796:
787:
774:
765:
752:
737:
736:
735:
733:
726:
720:
716:
714:
713:agrochemicals
710:
706:
701:
699:
695:
687:
683:
682:hydrogenation
679:
672:Hydrogenation
671:
640:
627:
607:
594:
558:
548:
540:
532:
518:
509:
494:
493:
492:
490:
483:
479:
470:
463:
438:
437:
436:
434:
430:
429:carbonylation
426:
422:
421:methyl iodide
418:
414:
411:
407:
406:catalytically
399:
394:
390:
388:
384:
383:carbonylation
381:by catalytic
380:
376:
368:
366:
360:
358:
356:
348:
347:electrophilic
344:
328:
324:
320:
316:
313:
307:Metallacycles
306:
300:
296:
294:
286:
284:
282:
279:
275:
267:
265:
263:
259:
255:
243:
239:
236:
228:
226:
200:
188:
184:
180:
176:
172:
168:
164:
160:
152:
150:
120:
119:carbonylation
108:
96:
88:
86:
83:
75:
73:
71:
67:
66:hydrogenation
63:
58:
56:
52:
48:
47:chemical bond
45:
41:
38:containing a
37:
33:
29:
21:
1870:Bond unknown
1451:
1153:
1149:
1142:
1117:
1113:
1107:
1088:
1082:
1073:
1059:(1): 73–91.
1056:
1050:
1044:
1028:
1013:
1008:
983:
980:Inorg. Chem.
978:
968:
951:
947:
941:
922:
905:
901:
761:nitrobenzene
732:Nitrobenzene
730:
702:
675:
487:
412:
403:
372:
364:
310:
290:
271:
268:Rhodium(III)
252:) catalyzes
232:
156:
92:
79:
59:
27:
26:
379:acetic acid
295:reactions.
229:Rhodium(II)
893:References
451:+ CO → (CH
343:azobenzene
293:borylation
287:Rhodium(V)
217:(L = CO, C
153:Rhodium(I)
89:Rhodium(0)
1851:to carbon
653:aldehydes
258:porphyrin
238:rhodocene
189:(RhCl(PPh
64:, olefin
51:catalysts
32:chemistry
1886:Category
1134:19746594
1000:18161963
853:PhNHCOPh
809:→
680:for the
559:→
1669:
315:rhodium
262:methane
40:rhodium
30:is the
1841:Legend
1204:carbon
1132:
1095:
1036:
998:
929:
528:alkene
181:, and
105:, and
44:carbon
482:Tppts
419:with
410:anion
248:(OAc)
1130:PMID
1093:ISBN
1034:ISBN
996:PMID
927:ISBN
749:PhNO
711:and
688:of H
404:The
373:The
201:)RhL
145:(CO)
141:, Rh
137:(CO)
129:(CO)
113:(CO)
109:, Rh
101:(CO)
97:, Rh
1815:CEs
1810:CCf
1805:CBk
1800:CCm
1795:CAm
1790:CPu
1785:CNp
1775:CPa
1770:CTh
1749:CYb
1744:CTm
1739:CEr
1734:CHo
1729:CDy
1724:CTb
1719:CGd
1714:CEu
1709:CSm
1704:CPm
1699:CNd
1694:CPr
1689:CCe
1684:CLa
1664:Og
1661:Ts
1658:Lv
1655:Mc
1652:Fl
1649:Nh
1646:Cn
1643:Rg
1640:Ds
1637:Mt
1634:Hs
1631:Bh
1627:CSg
1623:Db
1620:Rf
1604:CRa
1600:Fr
1595:Rn
1591:CAt
1586:CPo
1581:CBi
1576:CPb
1571:CTl
1566:CHg
1561:CAu
1556:CPt
1551:CIr
1546:COs
1541:CRe
1531:CTa
1526:CHf
1521:CLu
1509:CBa
1504:CCs
1497:CXe
1487:CTe
1482:CSb
1477:CSn
1472:CIn
1467:CCd
1462:CAg
1457:CPd
1452:CRh
1447:CRu
1442:CTc
1437:CMo
1432:CNb
1427:CZr
1415:CSr
1410:CRb
1403:CKr
1398:CBr
1393:CSe
1388:CAs
1383:CGe
1378:CGa
1373:CZn
1368:CCu
1363:CNi
1358:CCo
1353:CFe
1348:CMn
1343:CCr
1333:CTi
1328:CSc
1321:CCa
1309:CAr
1304:CCl
1289:CSi
1284:CAl
1279:CMg
1274:CNa
1268:Ne
1239:CBe
1234:CLi
1228:He
1158:doi
1122:doi
1061:doi
1018:doi
988:doi
956:doi
952:113
649:CHO
624:RCH
591:PPh
571:HRh
506:RHC
455:CO)
431:of
427:by
413:cis
333:·3H
323:azo
244:(Rh
225:).
53:in
34:of
1888::
1830:No
1825:Md
1820:Fm
1780:CU
1765:Ac
1616:Lr
1536:CW
1492:CI
1422:CY
1338:CV
1316:CK
1299:CS
1294:CP
1264:CF
1259:CO
1254:CN
1249:CC
1244:CB
1218:CH
1154:15
1152:.
1128:.
1118:41
1116:.
1057:13
1055:.
994:.
984:47
950:.
913:^
866:CO
840:16
832:CO
815:Rh
804:CO
715:.
700:.
637:CH
578:CO
537:CO
515:CH
476:=
447:CH
443:CO
439:CH
435:.
389:.
283:.
264:.
209:Cl
199:Cp
177:,
173:,
169:,
165:,
125:Cl
115:16
103:12
72:.
57:.
1195:e
1188:t
1181:v
1164:.
1160::
1136:.
1124::
1101:.
1067:.
1063::
1020::
1002:.
990::
975:3
962:.
958::
935:.
870:2
861:2
857:+
835:)
829:(
819:6
800:3
797:+
788:6
784:H
775:6
771:C
766:+
753:2
690:2
641:2
628:2
608:3
603:)
595:3
587:(
581:)
575:(
549:2
545:H
541:+
533:+
519:2
510:=
484:.
474:3
459:O
457:2
453:3
449:3
445:2
441:3
351:3
339:3
335:2
331:3
250:4
246:2
223:4
221:H
219:2
215:4
213:L
211:2
207:2
203:2
195:3
193:)
191:3
147:8
143:2
139:8
135:2
131:4
127:2
123:2
111:6
99:4
42:-
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