Record 9752 View: Standard | Glossary HistCite Guide |
Author(s): Chen SN; Wu WY; Tsai FY
Title: Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by a reusable palladium(II)/cationic bipyridyl system in water
Source: TETRAHEDRON 64 (35): 8164-8168
Date: 2008 AUG 25
Document Type: Journal : Article
DOI:
Language: English
Comment:
Address: Natl Taipei Univ Technol, Inst Organ & Polymer Mat, Taipei 106, Taiwan.
Reprint: Tsai, FY, Natl Taipei Univ Technol, Inst Organ & Polymer Mat, Taipei
106, Taiwan. E-mail: fuyutsai@ntut.edu.tw
Author Keywords: Hiyama reaction; water-soluble catalyst; reusable; cross-coupling;
biaryls
KeyWords Plus: CROSS-COUPLING REACTIONS; HYPERVALENT SILOXANE DERIVATIVES; MILD
AEROBIC CONDITIONS; PALLADIUM CATALYSTS; STILLE REACTION; ORGANIC
ELECTROPHILES; UNSYMMETRICAL BIARYLS; EFFICIENT CATALYST; SODIUM-
HYDROXIDE; SUZUKI
Abstract: A Pd(NH3)(2)Cl-2/cationic bipyridyl catalytic system catalyzed the cross-coupling reaction of aryl bromides with arylsiloxanes in water under aerobic conditions in the presence of NaOH to afford biaryls in good to high yields. The reaction was performed at 120 degrees C and the loading amount of catalyst can be as low as 0.001 mol %. After extraction, the residual aqueous phase can be reused several times with only a slight decrease in activity. (C) 2008 Elsevier Ltd. All rights reserved.
Cited References: ACKERMANN L, 2006, ORG LETT, V8, P3457 ALACID E, 2006, ADV SYNTH CATAL, V348, P2085 ALACID E, 2006, ADV SYNTH CATAL, V348, P945 ASTRUC D, 2007, INORG CHEM, V46, P1884 BARNARD C, 2008, PLATINUM MET REV, V52, P38 BELLER M, 2004, TRANSITION METALS OR BYRON DJ, 1966, J CHEM SOC, P840 CORNILS B, 2002, APPL HOMOGENEOUS CAT CORREIA R, 2001, J ORG CHEM, V66, P7159 DELAMARE PBD, 1962, J CHEM SOC, P3784 DEMARK SE, 2003, ORG LETT, V5, P1357 DEMEIJERE A, 2004, METAL CATALYZED CROS DENMARK SE, 2002, ACCOUNTS CHEM RES, V35, P835 DENMARK SE, 2002, ORG LETT, V4, P3771 DENMARK SE, 2003, ALDRICHIM ACTA, V36, P75 DESOUZA MVN, 2006, CURR ORG SYNTH, V3, P313 DIEDERICH F, 1998, METAL CATALYZED CROS ESPINET P, 2004, ANGEW CHEM INT EDIT, V43, P4704 FARINA V, 1993, J ORG CHEM, V58, P5434 GORDILLO A, 2006, ORG LETT, V8, P3517 GORDILLO A, 2007, CHEM COMMUN, P4056 GOUDA K, 1996, J ORG CHEM, V61, P7232 HAGIO H, 2006, ORG LETT, V8, P375 HAGIWARA E, 1997, TETRAHEDRON LETT, V38, P439 HANDY CJ, 2005, TETRAHEDRON, V61, P12201 HATANAKA Y, 1988, J ORG CHEM, V53, P918 HATANAKA Y, 1989, CHEM LETT OCT, P1711 HIYAMA T, 2002, J ORGANOMET CHEM, V653, P58 HUANG TS, 2002, TETRAHEDRON LETT, V43, P403 JAYANTH TT, 2005, ORG LETT, V7, P2921 JU JH, 2006, TETRAHEDRON LETT, V47, P8673 KOSUGI M, 2002, J ORGANOMET CHEM, V653, P50 LEADBEATER NE, 1999, TETRAHEDRON, V55, P11889 LEE HM, 2000, ORG LETT, V2, P2053 LEREBOURS R, 2005, SYNTHESIS-STUTT 0902, P2287 LI JH, 2005, SYNTHESIS-STUTT 1116, P3039 LITTKE AF, 2000, J AM CHEM SOC, V122, P4020 LIU SF, 2007, J MOL CATAL A-CHEM, V270, P1 LU JP, 2004, MACROMOLECULES, V37, P2442 MANOSO AS, 2004, J ORG CHEM, V69, P8305 MCELROY WT, 2003, ORG LETT, V5, P4779 MINO T, 2005, J ORG CHEM, V70, P2191 MINO T, 2006, J ORG CHEM, V71, P9499 MIYAURA N, 1995, CHEM REV, V95, P2457 MIYAURA N, 2002, TOP CURR CHEM, P219 MOWERY ME, 1999, J ORG CHEM, V64, P1684 MOWERY ME, 1999, J ORG CHEM, V64, P3266 MOWERY ME, 1999, ORG LETT, V1, P2137 MURATA M, 2001, SYNTHESIS-STUTTG NOV, P2231 MURATA M, 2006, SYNLETT 0105, P118 MUTULE G, 2005, TETRAHEDRON, V61, P11168 NAJERA C, 2003, ORG LETT, V5, P1451 NAKAMICHI N, 2003, J ORG CHEM, V68, P8272 NEGISHI EI, 2002, HDB ORGANOPALLADIUM OKI AR, 1995, SYNTHETIC COMMUN, V25, P4093 PHAN NTS, 2006, ADV SYNTH CATAL, V348, P609 PIERRAT P, 2005, ORG LETT, V7, P697 PRUKALA W, 2007, TETRAHEDRON, V63, P1107 RIGGLEMAN S, 2003, J ORG CHEM, V68, P8106 SAHOO AK, 2004, ADV SYNTH CATAL, V346, P1715 SEGANISH WM, 2004, J ORG CHEM, V69, P1137 SEGANISH WM, 2004, J ORG CHEM, V69, P6790 SHI SY, 2007, J ORG CHEM, V72, P5927 SHIBATA K, 1997, CHEM COMMUN 0721, P1309 SRIMANI D, 2007, ORG LETT, V9, P3639 STANFORTH SP, 1998, TETRAHEDRON, V54, P263 STILLE JK, 1986, ANGEW CHEM INT EDIT, V25, P508 SUZUKI A, 1999, J ORGANOMET CHEM, V576, P147 SUZUKI A, 2002, J ORGANOMET CHEM, V653, P83 TAO B, 2004, J ORG CHEM, V69, P4330 TSAI FY, 2007, TETRAHEDRON, V63, P4304 UEURA K, 2005, ORG LETT, V7, P2229 WANG DP, 2006, CHINESE J ORG CHEM, V26, P19 WANG YH, 2007, CHEM LETT, P1492 WILL G, 1999, J PHYS CHEM B, V103, P8067 WOLF C, 2003, SYNTHESIS-STUTT 0918, P2069 WOLF C, 2004, ORG LETT, V6, P1147 WOLFE JP, 1999, J AM CHEM SOC, V121, P9550 WU WY, 2006, TETRAHEDRON LETT, V47, P9267 YIN LX, 2007, CHEM REV, V107, P133 |