| Record 9523 View: Standard | Glossary HistCite Guide |
|
Author(s): Kondo T
Title: On inventing catalytic reactions via ruthena-or rhodacyclic intermediates for atom economy
Source: SYNLETT (5): 629-644
Date: 2008 MAR 18
Document Type: Journal : Review
DOI:
Language: English
Comment:
Address: Kyoto Univ, Grad Sch Engn, Dept Engn & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6168510, Japan.
Reprint: Kondo, T, Kyoto Univ, Grad Sch Engn, Dept Engn & Hydrocarbon Chem,
Nishikyo Ku, Kyoto 6168510, Japan. E-mail: teruyuki@scl.kyoto-u.ac.jp
Author Keywords: ruthenium; rhodium; catalyst; cocyclization; C-C bond cleavage
KeyWords Plus: PAUSON-KHAND REACTION; TRANSITION-METAL-COMPLEXES; C-C BOND; CARBON-
CARBON BOND; 2+2+2 CYCLOADDITION REACTIONS; N-SUBSTITUTED MALEIMIDES;
SYNDIOTACTIC-SPECIFIC POLYMERIZATION; CATIONIC PALLADIUM(II) COMPOUNDS;
HIGHLY SELECTIVE DIMERIZATION; TITANIUM ARYLOXIDE COMPOUNDS
Abstract: Novel catalytic reactions via ruthena-or rhodacyclic intermediates have been developed by our research group. We initiated our study from (1) ruthenium-catalyzed [2+2] cycloaddition of alkynes with alkenes, followed by developing (2) intramolecular Pauson-Khand-type reaction of 1,6-enynes, (3) hydroquinone synthesis, (4) cyclocotrimerization reactions, and (5) codimerization of styrenes with ethylene. Another approach to construct novel functional monomers, such as cyclopentenones, pyranopyrandiones, and substituted phenols, involves cleavage of carbon-carbon bonds in cyclobutenediones, cyclopropenones, and cyclobutenones. All reactions may proceed with high atom-efficiency via ruthena-or rhodacyclic intermediates, represented by ruthenacyclopentene, (maleoyl)ruthenium, and rhodacyclopentenone intermediates. In addition, rhodium-catalyzed [2+2+2] cocyclization of alkynes with isocyanates as well as novel ruthenium-catalyzed [2+2+1] cocyclization of alkynes, isocyanates, and carbon monoxide have been disclosed.
Cited References: AGENET N, 2007, J AM CHEM SOC, V129, P8860 AGENET N, 2007, ORG REACTIONS, V68, P1 ALCAIDE B, 2004, EUR J ORG CHEM ALDERSON T, 1965, J AM CHEM SOC, V87, P5638 ALJARALLAH AM, 1992, CATAL TODAY, V14, P1 BABA A, 1976, CHEM LETT, P11 BABA A, 1976, J ORGANOMET CHEM, V110, P121 BALAICH GJ, 1993, J AM CHEM SOC, V115, P1581 BALDWIN JE, 1991, COMPREHENSIVE ORGANI, V5, P63 BARLOW MG, 1970, J ORGANOMET CHEM, V21, P215 BARROW M, 2001, J CHEM SOC DALTON, P1352 BARTHELEMY P, 1985, NOUV J CHIM, V9, P173 BAYERSDORFER R, 1998, J ORGANOMET CHEM, V552, P187 BAYSDON SL, 1982, ORGANOMETALLICS, V1, P771 BERK SC, 1994, J AM CHEM SOC, V116, P8593 BIRD CW, 1967, J CHEM SOC C, P1862 BIRD CW, 1974, J ORGANOMET CHEM, V69, P311 BISHOP KC, 1976, CHEM REV, V76, P461 BOGDANOVIC B, 1979, ADV ORGANOMET CHEM, V17, P105 BONAGA LVR, 2004, TETRAHEDRON, V60, P9795 BOSMANN A, 2001, ANGEW CHEM INT EDIT, V40, P2697 BRITOVSEK GJP, 1993, CHEM COMMUN, P1632 BRITOVSEK GJP, 1996, J MOL CATAL A-CHEM, V110, P77 BROWN LD, 1978, J AM CHEM SOC, V100, P8232 BRUMMOND KM, 2005, J ORG CHEM, V70, P1745 BURGER BJ, 1988, J AM CHEM SOC, V110, P3134 BURGESS J, 1975, J CHEM SOC DALTON, P2579 BURRELL RC, 1996, J AM CHEM SOC, V118, P4218 CAMPORA J, 1999, COORDIN CHEM REV, V193, P207 CAO H, 2005, J AM CHEM SOC, V127, P933 CARBONAR.A, 1968, TETRAHEDRON LETT, P5129 CARROLL WE, 1978, J CHEM SOC DA, P1472 CEDER R, 1994, J MOL CATAL, V92, P127 CHALK AJ, 1972, J AM CHEM SOC, V94, P5928 CHAPPELL SD, 1982, POLYHEDRON, V1, P739 CHATANI N, 1987, J ORG CHEM, V52, P4408 CHATANI N, 1994, J AM CHEM SOC, V116, P6049 CHATANI N, 1999, J ORGANOMET CHEM, V579, P177 CHIUSOLI GP, 1987, J MOL CATAL, V41, P75 CHIUSOLI GP, 1992, J CHEM SOC P1, P1399 CHOPADE PR, 2006, ADV SYNTH CATAL, V348, P2307 CHRISTOFFERS J, 1996, J AM CHEM SOC, V118, P4715 CRABTREE RH, 1985, CHEM REV, P85 CRIMMINS MT, 1991, COMPREHENSIVE ORGANI, V5, P123 CROWE WE, 1996, J AM CHEM SOC, V118, P1557 DANHEISER RL, 1984, J ORG CHEM, V49, P1672 DANHEISER RL, 1988, TETRAHEDRON LETT, V29, P4917 DANHEISER RL, 1994, J ORG CHEM, V59, P5514 DAUTER Z, 1985, J CHEM SOC DA, P1235 DAWANS F, 1971, TETRAHEDRON LETT, V22, P1943 DIERCKS R, 1998, J AM CHEM SOC, V120, P8247 DIVER T, 2004, CHEM REV, V104, P1317 DIVERSI P, 1987, J MOL CATAL, V40, P267 DONKERVOORT JG, 1996, TETRAHEDRON, V52, P7391 DOYLE MJ, 1976, J CHEM SOC CHEM COMM, P376 DUANG HA, 2004, J AM CHEM SOC, V126, P11438 EARL RA, 1983, J AM CHEM SOC, V105, P6991 EARL RA, 1984, J ORG CHEM, V49, P4786 EGGELING EB, 2000, J ORG CHEM, V65, P8857 EICHER T, 1975, TOP CURR CHEM, V57, P1 EVANS FA, 2003, MODERN RHODIUM CATAL, P129 FICHTEMAN WL, 1968, J ORGANOMET CHEM, V12, P249 FLYNN ST, 1985, J MOL CATAL, V32, P101 FOERSTNER J, 2000, ORGANOMETALLICS, V19, P2108 FRANCIO G, 2002, J AM CHEM SOC, V124, P736 FRASER AR, 1973, J AM CHEM SOC, V95, P597 FRUHAUF HW, 1997, CHEM REV, V97, P523 FUKUYAMA T, 2005, ORG LETT, V7, P5781 FURSTNER A, 1998, ALKENE METATHESSI OR FURSTNER A, 2000, ANGEW CHEM INT EDIT, V39, P3012 GADE LH, 2000, CHEM-EUR J, V6, P692 GALDI N, 2006, J MOL CATAL A-CHEM, V243, P106 GANDON V, 2006, CHEM COMMUN, P2209 GANDON V, 2006, J AM CHEM SOC, V128, P8509 GENY A, 2007, CHEM-EUR J, V13, P5408 GEVORGYAN V, 1999, J AM CHEM SOC, V121, P6391 GEVORGYAN V, 2001, J ORG CHEM, V66, P2743 GEVORGYAN V, 2001, J ORG CHEM, V66, P2835 GIBSON SE, 1999, ADV ORGANOMET CHEM, V44, P275 GIBSON SE, 2003, ANGEW CHEM INT EDIT, V42, P1800 GIBSON SE, 2004, J ORGANOMET CHEM, V689, P3873 GIBSON SE, 2005, ANGEW CHEM INT EDIT, V44, P3022 GOROBETS NY, 2004, TETRAHEDRON, V60, P8633 GRENOUILLET P, 1984, ORGANOMETALLICS, V3, P1130 GRIGG R, 1998, J CHEM SOC P1, P1365 GRUBBS RH, 1998, TETRAHEDRON, V54, P4413 GRUTTERS MMP, 2006, J AM CHEM SOC, V128, P7414 HAJELA S, 1994, ORGANOMETALLICS, V13, P1147 HAJRA S, 2005, TETRAHEDRON LETT, V46, P8599 HANNA TA, 1996, J ORG CHEM, V61, P4532 HARTWIG JF, 1991, J AM CHEM SOC, V113, P6499 HEGEDUS LS, 1995, ORGANOMETALIC CHEM 2, V12, P741 HEGEDUS LS, 2009, TRANSITION METALS SY, P143 HENRICIOLIVE G, 1972, J ORGANOMET CHEM, V39, P201 HIGASHIMURA M, 2004, CHEM LETT, V33, P728 HOBERG H, 1981, ANGEW CHEM INT EDIT, V20, P876 HOBERG H, 1982, J ORGANOMET CHEM, V234, PC35 HOBERG H, 1983, J ORGANOMET CHEM, V252, P359 HOBERG YH, 1982, SYNTHESIS-STUTTGART, P324 HONG P, 1977, SYNTHESIS-STUTTGART, P50 HONG P, 1977, TETRAHEDRON LETT, V18, P1333 HOVESTAD NJ, 1999, ANGEW CHEM INT EDIT, V38, P1655 HUFFMAN MA, 1990, J AM CHEM SOC, V112, P8617 HUFFMAN MA, 1990, ORGANOMETALLICS, V9, P2194 HUFFMAN MA, 1991, J AM CHEM SOC, V113, P2771 HUFFMAN MA, 1992, ORGANOMETALLICS, V11, P255 HUFFMANN MA, 1993, J AM CHEM SOC, V155, P4895 IKEDA S, 1997, J AM CHEM SOC, V119, P4779 IKEDA S, 1998, J ORG CHEM, V63, P7026 INAGAKI S, 1976, J AM CHEM SOC, V98, P4054 JENNINGS PW, 1994, CHEM REV, V94, P2241 JEWELL CF, 1985, J AM CHEM SOC, V107, P6715 JIANG ZZ, 1990, J AM CHEM SOC, V112, P9655 JIANG ZZ, 1993, ORGANOMETALLICS, V12, P1406 JIN J, 2000, TETRAHEDRON, V56, P2145 JOHNSON ES, 1997, J AM CHEM SOC, V119, P7685 JUN CH, 2004, CHEM SOC REV, V33, P610 KABALKA GW, 2004, TETRAHEDRON LETT, V45, P2775 KALGUTKAR AS, 1996, J MED CHEM, V39, P1692 KANEDA K, 1988, J MOL CATAL, V48, P343 KAWAMOTO K, 1971, B CHEM SOC JPN, V44, P1239 KAWATA N, 1974, B CHEM SOC JPN, V47, P413 KONDO T, 1997, J AM CHEM SOC, V119, P6187 KONDO T, 1998, J AM CHEM SOC, V120, P5587 KONDO T, 2000, J AM CHEM SOC, V122, P6319 KONDO T, 2002, J AM CHEM SOC, V124, P6824 KONDO T, 2002, ORGANOMETALLICS, V21, P4564 KONDO T, 2004, ANGEW CHEM INT EDIT, V43, P5369 KONDO T, 2005, CHEM LETT, V34, P1462 KONDO T, 2006, J AM CHEM SOC, V128, P14816 KONDO T, 2006, TETRAHEDRON LETT, V47, P7107 KONDO T, 2007, ANGEW CHEM INT EDIT, V46, P5958 KONDO T, 2007, TETRAHEDRON LETT, V48, P2837 KOTHA S, 2005, EUR J ORG CHEM 1111, P4741 KRAMER B, 2002, ANGEW CHEM INT EDIT, V41, P2981 KREBS AW, 1965, ANGEW CHEM INT EDIT, V4, P10 KRETSCHMER WP, 1998, ORGANOMETALLICS, V17, P284 KRYSAN DJ, 1992, J AM CHEM SOC, V114, P1412 LAPOINTE AM, 1997, J AM CHEM SOC, V119, P906 LASCHAT S, 2005, SYNLETT 1017, P2547 LIANG YF, 1996, ORGANOMETALLICS, V15, P5284 LIEBESKIND LS, 1980, J ORGANOMET CHEM, V202, PC73 LIEBESKIND LS, 1984, J AM CHEM SOC, V106, P6451 LIEBESKIND LS, 1985, J ORGANOMET CHEM, V285, P305 LIEBESKIND LS, 1985, TETRAHEDRON, V41, P5839 LIEBESKIND LS, 1987, J AM CHEM SOC, V109, P5025 LIEBESKIND LS, 1989, TETRAHEDRON, V45, P3053 LINDHOLM L, 1986, FAM PRACT, V3, P3 LONGO P, 1995, MACROMOL CHEM PHYS, V196, P3015 MA SM, 2005, CHEM REV, V105, P2829 MACOMBER DW, 1988, ORGANOMETALLICS, V7, P1241 MATSUSHIMA Y, 1999, B CHEM SOC JPN, V72, P2475 MCGUIGGAN MF, 1982, INORG CHEM, V21, P2523 MILET A, 1997, INORG CHEM, V36, P3223 MITSUDO T, 1979, J ORG CHEM, V44, P4492 MITSUDO T, 1987, J ORGANOMET CHEM, V334, P157 MITSUDO T, 1992, J CHEM SOC CHEM COMM, P435 MITSUDO T, 1992, TETRAHEDRON LETT, V33, P341 MITSUDO T, 1994, ANGEW CHEM INT EDIT, V33, P580 MITSUDO T, 1999, J AM CHEM SOC, V121, P1839 MITSUDO T, 2004, J ORGANOMET CHEM, V689, P4530 MITSUDO T, 2006, CHEM REC, V6, P107 MITSUDO TA, 2007, P JPN ACAD B-PHYS, V83, P65 MONTEIRO AL, 1996, TETRAHEDRON LETT, V37, P1157 MOORE HW, 1986, CHEM REV, V86, P821 MOORE HW, 1995, ADV STR ORG, V4, P81 MOORE HW, CHEMTRACTS ORG CHEM MORI M, 1998, T ORGANOMET CHEM, V1, P133 MORI N, 1999, J AM CHEM SOC, V121, P2722 MORI N, 2001, CHEM COMMUN, P181 MORIMOTO T, 1997, J ORG CHEM, V62, P3762 MUKAI C, 2005, J ORG CHEM, V70, P7159 MUKAI C, 2006, ORG LETT, V8, P83 MULLER G, 1997, J MOL CATAL A-CHEM, V125, P97 MUNZ C, 1991, J ORGANOMET CHEM, V407, P413 MURAI S, 1993, NATURE, V366, P529 MURAKAMI M, 1996, J AM CHEM SOC, V118, P8285 MURAKAMI M, 1997, J AM CHEM SOC, V119, P9307 MURAKAMI M, 1999, ACTIVATION UNREACTIV, P97 NAKAHAMA H, 1999, PULM PHARMACOL THER, V12, P1 NANDI M, 1999, J AM CHEM SOC, V121, P9899 NEGISHI EI, 1996, CHEM REV, V96, P365 NELSON JE, 1989, ORGANOMETALLICS, V8, P2484 NISHIMURA T, 1999, J AM CHEM SOC, V121, P11010 NOMURA N, 1998, J AM CHEM SOC, V120, P459 NOYORI R, 1970, J AM CHEM SOC, V92, P5780 NOYORI R, 1972, CHEM LETT, P1189 OEVERING H, 1987, J AM CHEM SOC, V109, P3258 OHSHIRO Y, 1970, J ORG CHEM, V35, P2136 OHSHIRO Y, 1985, TETRAHEDRON LETT, V26, P3015 OJIMA I, 1996, CHEM REV, V96, P635 OLIVIERBOURBIGO.H, 2002, APPL HOMOGENEOUS CAT, V1, P253 OTSUKA S, 1976, ADV ORGANOMET CHEM, V14, P245 OZEROV OV, 1999, J AM CHEM SOC, V121, P7941 OZEROV OV, 2000, J AM CHEM SOC, V122, P6423 PARK H, 2002, J AM CHEM SOC, V124, P734 PARK KH, 2005, SYNLETT 0304, P545 PENG JJ, 2006, J MOL CATAL A-CHEM, V255, P16 PETERS JU, 1997, CHEM COMMUN 1021, P1983 PIERS WE, SYNLETT PILLAI SM, 1986, CHEM REV, V86, P353 PILLAI SM, 1993, J MOL CATAL, V84, P77 PONTRELLO JK, 2005, J AM CHEM SOC, V127, P14536 POTTS KT, 1974, CHEM REV, V74, P189 POULSEN CS, 2003, SYNTHESIS-STUTTG JAN, P1 RAJANBABU TV, 1999, CHEM-EUR J, V5, P1963 RAJANBABU TV, 2003, CHEM REV, V103, P2845 RIGBY JH, 2000, SYNLETT JAN, P1 ROSENTHAL U, 2007, CHEM SOC REV, V36, P719 RUBIN M, 2003, J ORG CHEM, V68, P6251 RYBCHINSKI B, 1999, ANGEW CHEM INT EDIT, V38, P870 SAITO S, 2000, CHEM REV, V100, P2901 SAITO S, 2000, J ORG CHEM, V65, P4338 SAITO T, 2003, HETEROCYCLES, V60, P1045 SCHMID R, 2003, J ORG CHEM, V68, P8339 SCHMID R, 2004, EUR J INORG CHE 0705, P2609 SCHMIDT AH, 1986, SYNTHESIS-STUTTGART, P961 SCHORE NE, 1988, CHEM REV, V88, P1081 SCHORE NE, 1991, COMPREHENSIVE ORGANI, V5, P1037 SEMMELHACK MF, 1986, STUD ORG CHEM AMSTER, V25, P21 SEN A, 1983, ORGANOMETALLICS, V2, P1059 SHING TKM, 1997, HOUBEN WEYL METHO B, V8, P898 SHU AYL, 1996, J ORGANOMET CHEM, V524, P87 SINGLETON DM, 1973, TETRAHEDRON LETT, P1245 SKUPINSKA J, 1991, CHEM REV, V91, P613 SONG LS, 1990, ORGANOMETALLICS, V9, P2792 SOREK Y, 1986, J CHEM SOC FARAD T 1, V82, P3431 SOREK Y, 1989, J CHEM SOC FARAD T 1, V85, P1169 STOCKIS A, 1980, J AM CHEM SOC, V102, P2952 STRUBING D, 2004, TRANSITION METALS OR, V1, P619 SUISENG C, 2006, ORGANOMETALLICS, V25, P571 SUISENG C, 2006, TOP CATAL, V37, P81 SUZUKI D, 2001, J AM CHEM SOC, V123, P7925 SUZUKI H, 1976, J AM CHEM SOC, V98, P8494 SUZUKI N, 1998, ORGANOMETALLICS, V17, P766 TAKAHASHI T, 1995, J CHEM SOC CHEM COMM, P361 TAKAHASHI T, 1998, J AM CHEM SOC, V120, P1672 TAKAHASHI T, 2002, J AM CHEM SOC, V124, P5059 TANAKA K, 2007, SYNLETT 0813, P1977 TANAKA R, 2002, J AM CHEM SOC, V124, P9682 TEMPEST PA, 1997, J AM CHEM SOC, V119, P7607 TORRES M, 2005, CURR ORG CHEM, V9, P1757 TRNKA TM, 2001, ACCOUNTS CHEM RES, V34, P18 TSUCHIMOTO T, 2003, CHEM COMMUN, P852 TSUDA T, 1997, ORGANOMETALLICS, V16, P932 TSUJITA H, 2007, ANGEW CHEM INT EDIT, V46, P5160 TSUKADA N, 1997, J AM CHEM SOC, V119, P8123 TSUKADA N, 2000, ORG LETT, V2, P655 UMEZAKI H, 1973, B CHEM SOC JPN, V46, P2230 URA Y, 2004, J MOL CATAL A-CHEM, V209, P35 URA Y, 2005, J MOL CATAL A-CHEM, V239, P166 URA Y, 2005, J ORG CHEM, V70, P6623 VARELA JA, 2003, CHEM REV, V103, P3787 VISSER JP, 1972, J ORGANOMET CHEM, V44, PC63 VOLLHARDT KPC, 1984, ANGEW CHEM INT EDIT, V23, P539 WARRENER RN, 1983, J CHEM SOC CHEM COMM, P1340 WEISSERMEL K, 2003, IND ORGANIC CHEM, P368 WEST R, 1980, OXOCARBONS WILKE G, 1988, ANGEW CHEM INT EDIT, V27, P185 WITULSKI B, 2000, CHEM COMMUN, P1965 WONG W, 1972, J CHEM SOC CHEM COMM, P672 WU G, 1987, ORGANOMETALLICS, V6 YAMAMOTO Y, 1998, J ORG CHEM, V63, P9610 YAMAMOTO Y, 1998, ORGANOMETALLICS, V17, P1910 YAMAMOTO Y, 2000, CHEM COMMUN, P549 YAMAMOTO Y, 2000, J AM CHEM SOC, V122, P4310 YAMAMOTO Y, 2001, J AM CHEM SOC, V123, P6372 YAMAMOTO Y, 2001, ORG LETT, V3, P2117 YAMAMOTO Y, 2002, J AM CHEM SOC, V124, P28 YAMAMOTO Y, 2004, J AM CHEM SOC, V126, P3712 YAMAMOTO Y, 2004, RUTHENIUM ORGANIC SY, P95 YAMAMOTO Y, 2005, CURR ORG CHEM, V9, P503 YAMAMOTO Y, 2005, J AM CHEM SOC, V127, P605 YANG WS, 2002, NAT MATER, V1, P253 YASUFUKU K, 1977, J ORGANOMET CHEM, V127, P197 YI CS, 2001, ORGANOMETALLICS, V20, P802 YOSHIDA Z, 1997, HOUBEN WEYL METHODS, V17, P2983 YU RT, 2006, J AM CHEM SOC, V128, P2782 ZAMBELLI A, 1995, MACROMOL S, V89, P373 ZHANG X, 2006, J POLYM SCI POL CHEM, V44, P304 ZHOU Z, 1990, J CHEM SOC CHEM COMM, P1632 |