Coupling of vinylic tellurides with alkynes catalyzed by palladium dichloride: Evaluation of synthetic and mechanistic details

C. Raminelli; Martin H. G. Prechtl; L. S. Santos; M. N. Eberlin; J. V. Comasseto

doi:10.1021/om049805w

Coupling of vinylic tellurides with alkynes catalyzed by palladium dichloride: Evaluation of synthetic and mechanistic details

C. Raminelli, Martin H. G. Prechtl, L. S. Santos, M. N. Eberlin, J. V. Comasseto

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

Under palladium dichloride catalysis, vinylic tellurides couple efficiently with alkynes with retention of the double-bond geometry. Herein we show that the amount of the PdCl2 catalyst can be reduced from 40 mol % to 10 mol % by using copper(II) chloride as an oxidizing agent. Under these conditions, an inert atmosphere is no longer required and the reaction occurs quite efficiently in the presence of air, leading to the enynes in 40-82% isolated yields. Mass and tandem mass spectrometric experiments using electrospray ionization were performed, and Pd-Te cationic intermediates were, for the first time, intercepted and transferred to the gas phase for structural characterization. An expanded catalytic cycle for this important method for enyne synthesis is proposed.

Originalsprog	Engelsk
Tidsskrift	Organometallics
Vol/bind	23
Udgave nummer	16
Sider (fra-til)	3990-3996
Antal sider	7
ISSN	0276-7333
DOI	https://doi.org/10.1021/om049805w
Status	Udgivet - 2004
Udgivet eksternt	Ja

Link til dokument

10.1021/om049805w

Citer dette

@article{d4c93595868d42cc97fd16694d04b329,

title = "Coupling of vinylic tellurides with alkynes catalyzed by palladium dichloride: Evaluation of synthetic and mechanistic details",

abstract = "Under palladium dichloride catalysis, vinylic tellurides couple efficiently with alkynes with retention of the double-bond geometry. Herein we show that the amount of the PdCl2 catalyst can be reduced from 40 mol % to 10 mol % by using copper(II) chloride as an oxidizing agent. Under these conditions, an inert atmosphere is no longer required and the reaction occurs quite efficiently in the presence of air, leading to the enynes in 40-82% isolated yields. Mass and tandem mass spectrometric experiments using electrospray ionization were performed, and Pd-Te cationic intermediates were, for the first time, intercepted and transferred to the gas phase for structural characterization. An expanded catalytic cycle for this important method for enyne synthesis is proposed.",

keywords = "electrospray mass-spectrometry atmospheric-pressure photoionization heck reaction antiinflammatory activity organic tellurides ionization mass z-enynes arylation enediynes chemistry Chemistry",

author = "C. Raminelli and Prechtl, {Martin H. G.} and Santos, {L. S.} and Eberlin, {M. N.} and Comasseto, {J. V.}",

note = "ISI Document Delivery No.: 841SD Times Cited: 51 Cited Reference Count: 58 Cited References: ALEXAKIS A, 1986, TETRAHEDRON LETT, V27, P1047, DOI 10.1016/S0040-4039(86)80044-2 ALIPRANTIS AO, 1994, J AM CHEM SOC, V116, P6985, DOI 10.1021/ja00094a083 Anastas PT, 2002, ACCOUNTS CHEM RES, V35, P686, DOI 10.1021/ar010065m Aramendia MA, 1999, J ORG CHEM, V64, P3592, DOI 10.1021/jo982210o BARROS SM, 1989, TETRAHEDRON LETT, V30, P7353, DOI 10.1016/S0040-4039(00)70695-2 Braga AL, 2002, TETRAHEDRON LETT, V43, P4399, DOI 10.1016/S0040-4039(02)00778-5 Braga AL, 2001, TETRAHEDRON LETT, V42, P8563, DOI 10.1016/S0040-4039(01)01867-6 Brown JM, 1996, ANGEW CHEM INT EDIT, V35, P657, DOI 10.1002/anie.199606571 Campbell I. B., 1994, ORGANOCOPPER REAGENT, P217 Cole R., 1997, ELECTROSPRAY IONIZAT COMASSETO JV, 1990, SYNTHETIC COMMUN, V20, P1681, DOI 10.1080/00397919008053089 Comasseto JV, 2000, ALDRICHIM ACTA, V33, P66 Cooks RG, 2001, ANAL CHEM, V73, P3646, DOI 10.1021/ac010284l COREY EJ, 1972, J AM CHEM SOC, V94, P6190, DOI 10.1021/ja00772a043 Dabdoub MJ, 2000, TETRAHEDRON LETT, V41, P437, DOI 10.1016/S0040-4039(99)02088-2 DABDOUB MJ, 1992, TETRAHEDRON LETT, V33, P2261, DOI 10.1016/S0040-4039(00)74184-0 DE MEIJERE A, 1994, ANGEW CHEM INT EDIT, V33, P2379, DOI 10.1002/anie.199423791 DEARAUJO MA, 1995, SYNLETT, P1145 EBERLIN MN, IN PRESS ANGEW CHEM Feichtinger D, 1998, J AM CHEM SOC, V120, P7125, DOI 10.1021/ja980004s Frosch W, 2000, J ORGANOMET CHEM, V601, P226, DOI 10.1016/S0022-328X(00)00067-X GALLI C, 1994, J ORG CHEM, V59, P6786, DOI 10.1021/jo00101a045 GRIEPRAMING J, 2002, ANGEW CHEM INT EDIT, V21, P2738 Hii KK, 1997, ANGEW CHEM INT EDIT, V36, P984, DOI 10.1002/anie.199709841 HIIRO T, 1987, ANGEW CHEM INT EDIT, V26, P1187, DOI 10.1002/anie.198711871 HORNING EC, 1974, J CHROMATOGR SCI, V12, P725 KAUFFMANN T, 1982, ANGEW CHEM INT EDIT, V21, P410, DOI 10.1002/anie.198204101 Kauppila TJ, 2002, ANAL CHEM, V74, P5470, DOI 10.1021/ac025659x Kotiaho T, 2000, J AM SOC MASS SPECTR, V11, P526, DOI 10.1016/S1044-0305(00)00116-1 Liu GS, 2002, TETRAHEDRON LETT, V43, P6791, DOI 10.1016/S0040-4039(02)01512-5 Meurer EC, 2003, ORG LETT, V5, P1391, DOI 10.1021/ol027439b Negishi E, 2003, CHEM REV, V103, P1979, DOI 10.1021/cr020377i Nishibayashi Y, 1996, J ORGANOMET CHEM, V526, P335, DOI 10.1016/S0022-328X(96)06561-8 Nishibayashi Y, 1996, J ORGANOMET CHEM, V507, P197, DOI 10.1016/0022-328X(95)05763-F Perrin DD, 1980, PURIFICATION LAB CHE Plattner DA, 2001, INT J MASS SPECTROM, V207, P125, DOI 10.1016/S1387-3806(01)00371-2 Ripa L, 1996, J ORG CHEM, V61, P7147, DOI 10.1021/jo960970y Robb DB, 2000, ANAL CHEM, V72, P3653, DOI 10.1021/ac0001636 Rossi R., 1995, ORG PREP P INT, V27, P129 Sabino AA, 2004, ANGEW CHEM INT EDIT, V43, P2514, DOI 10.1002/anie.200353076 SONOGASHIRA K, 1975, TETRAHEDRON LETT, P4467 Colton R, 1995, MASS SPECTROM REV, V14, P79, DOI 10.1002/mas.1280140203 Tsuji J., 1999, PALLADIUM REAGENTS C Tucci FC, 1996, J ORG CHEM, V61, P4975, DOI 10.1021/jo951547c UEMURA S, 1980, J ORGANOMET CHEM, V194, P277, DOI 10.1016/S0022-328X(00)96183-7 UEMURA S, 1992, J ORGANOMET CHEM, V423, pC9, DOI 10.1016/0022-328X(92)83033-E Wang Z, 2000, ORGANOMETALLICS, V19, P775, DOI 10.1021/om990670h WATSON SC, 1967, J ORGANOMET CHEM, V9, P165, DOI 10.1016/S0022-328X(00)92418-5 Zeni G, 2002, SYNLETT, P975 Zeni G, 2001, TETRAHEDRON LETT, V42, P8927, DOI 10.1016/S0040-4039(01)01984-0 Zeni G, 2003, SYNLETT, P579, DOI 10.1055/s-2003-37519 Zeni G, 2001, SYNLETT, P1473 Zeni G, 2003, TETRAHEDRON LETT, V44, P685, DOI 10.1016/S0040-4039(02)02659-X Zeni G, 2003, ACCOUNTS CHEM RES, V36, P731, DOI 10.1021/ar0202621 Zeni G, 2003, TETRAHEDRON LETT, V44, P1387, DOI 10.1016/S0040-4039(02)02879-4 Zeni G, 2001, TETRAHEDRON LETT, V42, P7921, DOI 10.1016/S0040-4039(01)01703-8 Zeni G, 1999, TETRAHEDRON LETT, V40, P4619, DOI 10.1016/S0040-4039(99)00773-X Zhang ZG, 2001, ORGANOMETALLICS, V20, P3724, DOI 10.1021/om0101994 Raminelli, C Prechtl, MHG Santos, LS Eberlin, MN Comasseto, JV Santos, Leonardo/A-7953-2008; Eberlin, Marcos/B-8106-2012; Prechtl, Martin/A-7416-2008 Santos, Leonardo/0000-0003-0908-0134; Prechtl, Martin/0000-0003-2155-8006 51 Amer chemical soc Washington",

year = "2004",

doi = "10.1021/om049805w",

language = "English",

volume = "23",

pages = "3990--3996",

journal = "Organometallics",

issn = "0276-7333",

number = "16",

}

TY - JOUR

T1 - Coupling of vinylic tellurides with alkynes catalyzed by palladium dichloride: Evaluation of synthetic and mechanistic details

AU - Raminelli, C.

AU - Prechtl, Martin H. G.

AU - Santos, L. S.

AU - Eberlin, M. N.

AU - Comasseto, J. V.

N1 - ISI Document Delivery No.: 841SD Times Cited: 51 Cited Reference Count: 58 Cited References: ALEXAKIS A, 1986, TETRAHEDRON LETT, V27, P1047, DOI 10.1016/S0040-4039(86)80044-2 ALIPRANTIS AO, 1994, J AM CHEM SOC, V116, P6985, DOI 10.1021/ja00094a083 Anastas PT, 2002, ACCOUNTS CHEM RES, V35, P686, DOI 10.1021/ar010065m Aramendia MA, 1999, J ORG CHEM, V64, P3592, DOI 10.1021/jo982210o BARROS SM, 1989, TETRAHEDRON LETT, V30, P7353, DOI 10.1016/S0040-4039(00)70695-2 Braga AL, 2002, TETRAHEDRON LETT, V43, P4399, DOI 10.1016/S0040-4039(02)00778-5 Braga AL, 2001, TETRAHEDRON LETT, V42, P8563, DOI 10.1016/S0040-4039(01)01867-6 Brown JM, 1996, ANGEW CHEM INT EDIT, V35, P657, DOI 10.1002/anie.199606571 Campbell I. B., 1994, ORGANOCOPPER REAGENT, P217 Cole R., 1997, ELECTROSPRAY IONIZAT COMASSETO JV, 1990, SYNTHETIC COMMUN, V20, P1681, DOI 10.1080/00397919008053089 Comasseto JV, 2000, ALDRICHIM ACTA, V33, P66 Cooks RG, 2001, ANAL CHEM, V73, P3646, DOI 10.1021/ac010284l COREY EJ, 1972, J AM CHEM SOC, V94, P6190, DOI 10.1021/ja00772a043 Dabdoub MJ, 2000, TETRAHEDRON LETT, V41, P437, DOI 10.1016/S0040-4039(99)02088-2 DABDOUB MJ, 1992, TETRAHEDRON LETT, V33, P2261, DOI 10.1016/S0040-4039(00)74184-0 DE MEIJERE A, 1994, ANGEW CHEM INT EDIT, V33, P2379, DOI 10.1002/anie.199423791 DEARAUJO MA, 1995, SYNLETT, P1145 EBERLIN MN, IN PRESS ANGEW CHEM Feichtinger D, 1998, J AM CHEM SOC, V120, P7125, DOI 10.1021/ja980004s Frosch W, 2000, J ORGANOMET CHEM, V601, P226, DOI 10.1016/S0022-328X(00)00067-X GALLI C, 1994, J ORG CHEM, V59, P6786, DOI 10.1021/jo00101a045 GRIEPRAMING J, 2002, ANGEW CHEM INT EDIT, V21, P2738 Hii KK, 1997, ANGEW CHEM INT EDIT, V36, P984, DOI 10.1002/anie.199709841 HIIRO T, 1987, ANGEW CHEM INT EDIT, V26, P1187, DOI 10.1002/anie.198711871 HORNING EC, 1974, J CHROMATOGR SCI, V12, P725 KAUFFMANN T, 1982, ANGEW CHEM INT EDIT, V21, P410, DOI 10.1002/anie.198204101 Kauppila TJ, 2002, ANAL CHEM, V74, P5470, DOI 10.1021/ac025659x Kotiaho T, 2000, J AM SOC MASS SPECTR, V11, P526, DOI 10.1016/S1044-0305(00)00116-1 Liu GS, 2002, TETRAHEDRON LETT, V43, P6791, DOI 10.1016/S0040-4039(02)01512-5 Meurer EC, 2003, ORG LETT, V5, P1391, DOI 10.1021/ol027439b Negishi E, 2003, CHEM REV, V103, P1979, DOI 10.1021/cr020377i Nishibayashi Y, 1996, J ORGANOMET CHEM, V526, P335, DOI 10.1016/S0022-328X(96)06561-8 Nishibayashi Y, 1996, J ORGANOMET CHEM, V507, P197, DOI 10.1016/0022-328X(95)05763-F Perrin DD, 1980, PURIFICATION LAB CHE Plattner DA, 2001, INT J MASS SPECTROM, V207, P125, DOI 10.1016/S1387-3806(01)00371-2 Ripa L, 1996, J ORG CHEM, V61, P7147, DOI 10.1021/jo960970y Robb DB, 2000, ANAL CHEM, V72, P3653, DOI 10.1021/ac0001636 Rossi R., 1995, ORG PREP P INT, V27, P129 Sabino AA, 2004, ANGEW CHEM INT EDIT, V43, P2514, DOI 10.1002/anie.200353076 SONOGASHIRA K, 1975, TETRAHEDRON LETT, P4467 Colton R, 1995, MASS SPECTROM REV, V14, P79, DOI 10.1002/mas.1280140203 Tsuji J., 1999, PALLADIUM REAGENTS C Tucci FC, 1996, J ORG CHEM, V61, P4975, DOI 10.1021/jo951547c UEMURA S, 1980, J ORGANOMET CHEM, V194, P277, DOI 10.1016/S0022-328X(00)96183-7 UEMURA S, 1992, J ORGANOMET CHEM, V423, pC9, DOI 10.1016/0022-328X(92)83033-E Wang Z, 2000, ORGANOMETALLICS, V19, P775, DOI 10.1021/om990670h WATSON SC, 1967, J ORGANOMET CHEM, V9, P165, DOI 10.1016/S0022-328X(00)92418-5 Zeni G, 2002, SYNLETT, P975 Zeni G, 2001, TETRAHEDRON LETT, V42, P8927, DOI 10.1016/S0040-4039(01)01984-0 Zeni G, 2003, SYNLETT, P579, DOI 10.1055/s-2003-37519 Zeni G, 2001, SYNLETT, P1473 Zeni G, 2003, TETRAHEDRON LETT, V44, P685, DOI 10.1016/S0040-4039(02)02659-X Zeni G, 2003, ACCOUNTS CHEM RES, V36, P731, DOI 10.1021/ar0202621 Zeni G, 2003, TETRAHEDRON LETT, V44, P1387, DOI 10.1016/S0040-4039(02)02879-4 Zeni G, 2001, TETRAHEDRON LETT, V42, P7921, DOI 10.1016/S0040-4039(01)01703-8 Zeni G, 1999, TETRAHEDRON LETT, V40, P4619, DOI 10.1016/S0040-4039(99)00773-X Zhang ZG, 2001, ORGANOMETALLICS, V20, P3724, DOI 10.1021/om0101994 Raminelli, C Prechtl, MHG Santos, LS Eberlin, MN Comasseto, JV Santos, Leonardo/A-7953-2008; Eberlin, Marcos/B-8106-2012; Prechtl, Martin/A-7416-2008 Santos, Leonardo/0000-0003-0908-0134; Prechtl, Martin/0000-0003-2155-8006 51 Amer chemical soc Washington

PY - 2004

Y1 - 2004

N2 - Under palladium dichloride catalysis, vinylic tellurides couple efficiently with alkynes with retention of the double-bond geometry. Herein we show that the amount of the PdCl2 catalyst can be reduced from 40 mol % to 10 mol % by using copper(II) chloride as an oxidizing agent. Under these conditions, an inert atmosphere is no longer required and the reaction occurs quite efficiently in the presence of air, leading to the enynes in 40-82% isolated yields. Mass and tandem mass spectrometric experiments using electrospray ionization were performed, and Pd-Te cationic intermediates were, for the first time, intercepted and transferred to the gas phase for structural characterization. An expanded catalytic cycle for this important method for enyne synthesis is proposed.

AB - Under palladium dichloride catalysis, vinylic tellurides couple efficiently with alkynes with retention of the double-bond geometry. Herein we show that the amount of the PdCl2 catalyst can be reduced from 40 mol % to 10 mol % by using copper(II) chloride as an oxidizing agent. Under these conditions, an inert atmosphere is no longer required and the reaction occurs quite efficiently in the presence of air, leading to the enynes in 40-82% isolated yields. Mass and tandem mass spectrometric experiments using electrospray ionization were performed, and Pd-Te cationic intermediates were, for the first time, intercepted and transferred to the gas phase for structural characterization. An expanded catalytic cycle for this important method for enyne synthesis is proposed.

KW - electrospray mass-spectrometry atmospheric-pressure photoionization heck reaction antiinflammatory activity organic tellurides ionization mass z-enynes arylation enediynes chemistry Chemistry

U2 - 10.1021/om049805w

DO - 10.1021/om049805w

M3 - Journal article

SN - 0276-7333

VL - 23

SP - 3990

EP - 3996

JO - Organometallics

JF - Organometallics

IS - 16

ER -