Reaction of Dess-Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditionsCitation formats

Standard

Reaction of Dess-Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions : Tetrahedron Letters. / Andreou, T.; Bures, J.; Vilarrasa, J.

In: Tetrahedron Letters, Vol. 51, 2010, p. 1863-1866.

Research output: Contribution to journalArticle

Harvard

APA

Vancouver

Author

Bibtex

@article{9f9ea8d286cb4f718befbe55e697b519,
title = "Reaction of Dess-Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions: Tetrahedron Letters",
abstract = "Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.",
keywords = "Pyridylselenanes Terminal double bonds alkyl aryl selenoxides organic-synthesis pyridylseleno group syn elimination oxidation ketones derivatives reagents acids ibx",
author = "T. Andreou and J. Bures and J. Vilarrasa",
note = "M1 - 14 ISI Document Delivery No.: 573NM Times Cited: 0 Cited Reference Count: 36 Cited References: ANDREOU T, 2005, ORG LETT, V7, P4083, DOI 10.1021/ol051200o BACK TG, 1999, ORGANOSELENIUM CHEM BACK TG, 2004, ANGEW CHEM INT EDIT, V43, P1268, DOI 10.1002/anie.200353128 BACK TG, 2005, J ORG CHEM, V70, P9230, DOI 10.1021/jo0512711 BARTON DHR, 1985, TETRAHEDRON, V41, P4359 BHALLA A, 2009, J ORGANOMET CHEM, V694, P179, DOI 10.1016/j.jorganchem.2008.10.020 BLAY G, 1991, J ORG CHEM, V56, P6172 BLAY G, 2004, J ORG CHEM, V69, P7294, DOI 10.1021/jo040189n BURES J, 2009, J ORG CHEM, V74, P2203, DOI 10.1021/jo802825e CLARK RD, 1976, J ORG CHEM, V41, P1396 DESS DB, 1983, J ORG CHEM, V48, P4155 DOHI T, 2009, CHEM COMMUN, P2073 ESTEBAN J, 2004, TETRAHEDRON LETT, V45, P5563, DOI 10.1016/j.tetlet.2004.06.002 GRIECO PA, 1976, J ORG CHEM, V41, P1485 IGLESIASARTEAGA MA, 2006, TETRAHEDRON LETT, V47, P8029, DOI 10.1016/j.tetlet.2006.09.078 LADZIATA U, 2007, SYNLETT 0301, P527, DOI 10.1055/s-2007-967983 LU L, 2008, J AM CHEM SOC, V130, P7253, DOI 10.1021/ja803012n MANCUSO AJ, 1978, J ORG CHEM, V43, P2480 MARTIN M, 2004, TETRAHEDRON LETT, V45, P5559, DOI 10.1016/j.tetlet.2004.06.001 MAS G, 2003, TETRAHEDRON LETT, V44, P8805, DOI 10.1016/j.tetlet.2003.09.199 MOORTHY JN, 2008, TETRAHEDRON LETT, V49, P80, DOI 10.1016/j.tetlet.2007.11.013 NAKANISHI W, 1981, CHEM LETT, P1353 NICOLAOU KC, 2002, J AM CHEM SOC, V124, P2221 NICOLAOU KC, 2004, J AM CHEM SOC, V126, P5192, DOI 10.1021/ja0400382 PRAKASH O, 2004, TETRAHEDRON LETT, V45, P9065, DOI 10.1016/j.tetlet.2004.10.037 REICH HJ, 1978, J ORG CHEM, V43, P1697 RICHARDSON RD, 2007, ANGEW CHEM INT EDIT, V46, P6529, DOI 10.1002/anie.200702313 SAYAMA S, 2000, TETRAHEDRON LETT, V41, P5557 SHARPLESS KB, 1975, J ORG CHEM, V40, P947 TENBRINK GJ, 2001, J ORG CHEM, V66, P2429 TODO H, 1992, CHEM LETT, P1677 TOSHIMITSU A, 1984, J ORG CHEM, V49, P3796 TOSHIMITSU A, 1988, J CHEM SOC P1, P2113 TOSHIMITSU A, 2007, E EROS ENCY REAGENTS UEMURA S, 2005, PHOSPHORUS SULFUR, V180, P721, DOI 10.1080/10426500590907444 UYANIK M, 2009, CHEM COMMUN, P2086, DOI 10.1039/b823399c Andreou, Thanos Bures, Jordi Vilarrasa, Jaume Government of Spain (Madrid) [SAF02-02728, CrQ2006-15393]; Generalitat de Catalunya (Barcelona) ; Fundacio Bosch Gimpera-UB This work was partially funded by the Government of Spain (Madrid) via Grants SAF02-02728 and CrQ2006-15393. T.A. received a doctorate studentship (IGSoC program) from the Generalitat de Catalunya (Barcelona, 2003-2006) and later a studentship via Fundacio Bosch Gimpera-UB for one year. Experiments of Laia Esteban, when she was a DEA student ill our Department, deserve to be mentioned. Thanks are due to Francisco Cardenas, UB NMR Service, for registering the <SUP>77</SUP>Se NMR spectra. Pergamon-elsevier science ltd Oxford",
year = "2010",
doi = "10.1016/j.tetlet.2010.02.002",
language = "English",
volume = "51",
pages = "1863--1866",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier BV",

}

RIS

TY - JOUR

T1 - Reaction of Dess-Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions

T2 - Tetrahedron Letters

AU - Andreou, T.

AU - Bures, J.

AU - Vilarrasa, J.

N1 - M1 - 14 ISI Document Delivery No.: 573NM Times Cited: 0 Cited Reference Count: 36 Cited References: ANDREOU T, 2005, ORG LETT, V7, P4083, DOI 10.1021/ol051200o BACK TG, 1999, ORGANOSELENIUM CHEM BACK TG, 2004, ANGEW CHEM INT EDIT, V43, P1268, DOI 10.1002/anie.200353128 BACK TG, 2005, J ORG CHEM, V70, P9230, DOI 10.1021/jo0512711 BARTON DHR, 1985, TETRAHEDRON, V41, P4359 BHALLA A, 2009, J ORGANOMET CHEM, V694, P179, DOI 10.1016/j.jorganchem.2008.10.020 BLAY G, 1991, J ORG CHEM, V56, P6172 BLAY G, 2004, J ORG CHEM, V69, P7294, DOI 10.1021/jo040189n BURES J, 2009, J ORG CHEM, V74, P2203, DOI 10.1021/jo802825e CLARK RD, 1976, J ORG CHEM, V41, P1396 DESS DB, 1983, J ORG CHEM, V48, P4155 DOHI T, 2009, CHEM COMMUN, P2073 ESTEBAN J, 2004, TETRAHEDRON LETT, V45, P5563, DOI 10.1016/j.tetlet.2004.06.002 GRIECO PA, 1976, J ORG CHEM, V41, P1485 IGLESIASARTEAGA MA, 2006, TETRAHEDRON LETT, V47, P8029, DOI 10.1016/j.tetlet.2006.09.078 LADZIATA U, 2007, SYNLETT 0301, P527, DOI 10.1055/s-2007-967983 LU L, 2008, J AM CHEM SOC, V130, P7253, DOI 10.1021/ja803012n MANCUSO AJ, 1978, J ORG CHEM, V43, P2480 MARTIN M, 2004, TETRAHEDRON LETT, V45, P5559, DOI 10.1016/j.tetlet.2004.06.001 MAS G, 2003, TETRAHEDRON LETT, V44, P8805, DOI 10.1016/j.tetlet.2003.09.199 MOORTHY JN, 2008, TETRAHEDRON LETT, V49, P80, DOI 10.1016/j.tetlet.2007.11.013 NAKANISHI W, 1981, CHEM LETT, P1353 NICOLAOU KC, 2002, J AM CHEM SOC, V124, P2221 NICOLAOU KC, 2004, J AM CHEM SOC, V126, P5192, DOI 10.1021/ja0400382 PRAKASH O, 2004, TETRAHEDRON LETT, V45, P9065, DOI 10.1016/j.tetlet.2004.10.037 REICH HJ, 1978, J ORG CHEM, V43, P1697 RICHARDSON RD, 2007, ANGEW CHEM INT EDIT, V46, P6529, DOI 10.1002/anie.200702313 SAYAMA S, 2000, TETRAHEDRON LETT, V41, P5557 SHARPLESS KB, 1975, J ORG CHEM, V40, P947 TENBRINK GJ, 2001, J ORG CHEM, V66, P2429 TODO H, 1992, CHEM LETT, P1677 TOSHIMITSU A, 1984, J ORG CHEM, V49, P3796 TOSHIMITSU A, 1988, J CHEM SOC P1, P2113 TOSHIMITSU A, 2007, E EROS ENCY REAGENTS UEMURA S, 2005, PHOSPHORUS SULFUR, V180, P721, DOI 10.1080/10426500590907444 UYANIK M, 2009, CHEM COMMUN, P2086, DOI 10.1039/b823399c Andreou, Thanos Bures, Jordi Vilarrasa, Jaume Government of Spain (Madrid) [SAF02-02728, CrQ2006-15393]; Generalitat de Catalunya (Barcelona) ; Fundacio Bosch Gimpera-UB This work was partially funded by the Government of Spain (Madrid) via Grants SAF02-02728 and CrQ2006-15393. T.A. received a doctorate studentship (IGSoC program) from the Generalitat de Catalunya (Barcelona, 2003-2006) and later a studentship via Fundacio Bosch Gimpera-UB for one year. Experiments of Laia Esteban, when she was a DEA student ill our Department, deserve to be mentioned. Thanks are due to Francisco Cardenas, UB NMR Service, for registering the <SUP>77</SUP>Se NMR spectra. Pergamon-elsevier science ltd Oxford

PY - 2010

Y1 - 2010

N2 - Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

AB - Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR'CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR'CHCH2Se(OAc)(2)Py, seem to be formed. Treatment of these intermediates with aqueous NaHCO3 gives rise to irreversible hydrolysis and elimination to terminal alkenes. As the OH/SePy exchange can be performed in minutes, the overall process is an exceptionally efficient procedure for the dehydration of primary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Pyridylselenanes Terminal double bonds alkyl aryl selenoxides organic-synthesis pyridylseleno group syn elimination oxidation ketones derivatives reagents acids ibx

U2 - 10.1016/j.tetlet.2010.02.002

DO - 10.1016/j.tetlet.2010.02.002

M3 - Article

VL - 51

SP - 1863

EP - 1866

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

ER -