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Facile Ar-CF3 bond formation at Pd.: Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph]
被引:274
作者
:
Grushin, Vladimir V.
论文数:
0
引用数:
0
h-index:
0
机构:
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Grushin, Vladimir V.
[
1
]
Marshall, William J.
论文数:
0
引用数:
0
h-index:
0
机构:
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Marshall, William J.
[
1
]
机构
:
[1]
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2006年
/ 128卷
/ 39期
关键词
:
D O I
:
10.1021/ja064935c
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Facile and highly selective perfluoroalkyl-aryl reductive elimination from a metal center (Pd) has been demonstrated for the first time. At temperatures as low as 50-80 °C, [(Xantphos)Pd(Ph)CF3] undergoes remarkably clean decomposition to produce CF3Ph in high yield and selectivity. In contrast, analogous trifluoromethylpalladium aryls stabilized by rigid cis-chelating ligands such as dppe are completely unreactive at temperatures up to 130-140 °C. Decomposition of [(Ph3P)2Pd(Ph)CF3] in the presence of PhI in benzene at 60 °C does not produce PhCF3 but rather leads to [(Ph3P)2Pd(Ph)I] and [Ph4P]+[(Ph3P)Pd(CF3)3]- in a 2:1 ratio with high selectivity. Copyright © 2006 American Chemical Society.
引用
收藏
页码:12644 / 12645
页数:2
相关论文
共 28 条
[1]
BITE ANGLE DEPENDENCE OF THE RATE OF REDUCTIVE ELIMINATION FROM DIPHOSPHINE PALLADIUM COMPLEXES
[J].
BROWN, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Dyson Perrins Laboratory, Oxford, OX1 3QY, South Parks Road
BROWN, JM
;
GUIRY, PJ
论文数:
0
引用数:
0
h-index:
0
机构:
Dyson Perrins Laboratory, Oxford, OX1 3QY, South Parks Road
GUIRY, PJ
.
INORGANICA CHIMICA ACTA,
1994,
220
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:249
-259
[2]
Carbon-carbon bond-forming reductive elimination from arylpalladium complexes containing functionalized alkyl groups. Influence of ligand steric and electronic properties on structure, stability, and reactivity
[J].
Culkin, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Culkin, DA
;
Hartwig, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, JF
.
ORGANOMETALLICS,
2004,
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[3]
Molecular fluoro palladium complexes
[J].
Fraser, SL
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Fraser, SL
;
Antipin, MY
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Antipin, MY
;
Khroustalyov, VN
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Khroustalyov, VN
;
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Grushin, VV
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(20)
:4769
-4770
[4]
Organometallic chemistry of amidate complexes.: Accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II)
[J].
Fujita, Ken-ichi
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Fujita, Ken-ichi
;
Yamashita, Makoto
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yamashita, Makoto
;
Puschmann, Florian
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Puschmann, Florian
;
Alvarez-Falcon, Miguel Martinez
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Alvarez-Falcon, Miguel Martinez
;
Incarvito, Christopher D.
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Incarvito, Christopher D.
;
Hartwig, John F.
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, John F.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(28)
:9044
-9045
[5]
Grushin V., 2006, US Pat. Application Publ., Patent No. [US2006/0074261 A1, 20060074261]
[6]
Unexpected H2O-induced Ar-X activation with trifluoromethylpalladium(II) aryls
[J].
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
Grushin, VV
;
Marshall, WJ
论文数:
0
引用数:
0
h-index:
0
机构:
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
Marshall, WJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(14)
:4632
-4641
[7]
Thermal stability, decomposition paths, and Ph/Ph exchange reactions of [(Ph3P)2Pd(Ph)X] (X = I, Br, Cl, F, and HF2)
[J].
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Grushin, VV
.
ORGANOMETALLICS,
2000,
19
(10)
:1888
-1900
[8]
Cyclic diaryliodonium ions: old mysteries solved and new applications envisaged
[J].
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
Dupont Co, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Dupont Co, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Grushin, VV
.
CHEMICAL SOCIETY REVIEWS,
2000,
29
(05)
:315
-324
[9]
New entries to and new reactions of fluorocarbon ligands
[J].
Huang, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
Huang, DJ
;
Caulton, KG
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
Caulton, KG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(13)
:3185
-3186
[10]
Facile and reversible cleavage of C-F bonds.: Contrasting thermodynamic selectivity for Ru-CF2H vs F--Os=CFH
[J].
Huang, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Huang, DJ
;
Koren, PR
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Koren, PR
;
Folting, K
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Folting, K
;
Davidson, ER
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Davidson, ER
;
Caulton, KG
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Caulton, KG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(37)
:8916
-8931
←
1
2
3
→
共 28 条
[1]
BITE ANGLE DEPENDENCE OF THE RATE OF REDUCTIVE ELIMINATION FROM DIPHOSPHINE PALLADIUM COMPLEXES
[J].
BROWN, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Dyson Perrins Laboratory, Oxford, OX1 3QY, South Parks Road
BROWN, JM
;
GUIRY, PJ
论文数:
0
引用数:
0
h-index:
0
机构:
Dyson Perrins Laboratory, Oxford, OX1 3QY, South Parks Road
GUIRY, PJ
.
INORGANICA CHIMICA ACTA,
1994,
220
(1-2)
:249
-259
[2]
Carbon-carbon bond-forming reductive elimination from arylpalladium complexes containing functionalized alkyl groups. Influence of ligand steric and electronic properties on structure, stability, and reactivity
[J].
Culkin, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Culkin, DA
;
Hartwig, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, JF
.
ORGANOMETALLICS,
2004,
23
(14)
:3398
-3416
[3]
Molecular fluoro palladium complexes
[J].
Fraser, SL
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Fraser, SL
;
Antipin, MY
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Antipin, MY
;
Khroustalyov, VN
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Khroustalyov, VN
;
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
WILFRID LAURIER UNIV, DEPT CHEM, WATERLOO, ON N2L 3C5, CANADA
Grushin, VV
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(20)
:4769
-4770
[4]
Organometallic chemistry of amidate complexes.: Accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II)
[J].
Fujita, Ken-ichi
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Fujita, Ken-ichi
;
Yamashita, Makoto
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yamashita, Makoto
;
Puschmann, Florian
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Puschmann, Florian
;
Alvarez-Falcon, Miguel Martinez
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Alvarez-Falcon, Miguel Martinez
;
Incarvito, Christopher D.
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Incarvito, Christopher D.
;
Hartwig, John F.
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, John F.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(28)
:9044
-9045
[5]
Grushin V., 2006, US Pat. Application Publ., Patent No. [US2006/0074261 A1, 20060074261]
[6]
Unexpected H2O-induced Ar-X activation with trifluoromethylpalladium(II) aryls
[J].
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
Grushin, VV
;
Marshall, WJ
论文数:
0
引用数:
0
h-index:
0
机构:
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
EI DuPont Nemours & Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
Marshall, WJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(14)
:4632
-4641
[7]
Thermal stability, decomposition paths, and Ph/Ph exchange reactions of [(Ph3P)2Pd(Ph)X] (X = I, Br, Cl, F, and HF2)
[J].
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Grushin, VV
.
ORGANOMETALLICS,
2000,
19
(10)
:1888
-1900
[8]
Cyclic diaryliodonium ions: old mysteries solved and new applications envisaged
[J].
Grushin, VV
论文数:
0
引用数:
0
h-index:
0
机构:
Dupont Co, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Dupont Co, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
Grushin, VV
.
CHEMICAL SOCIETY REVIEWS,
2000,
29
(05)
:315
-324
[9]
New entries to and new reactions of fluorocarbon ligands
[J].
Huang, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
Huang, DJ
;
Caulton, KG
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
Caulton, KG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(13)
:3185
-3186
[10]
Facile and reversible cleavage of C-F bonds.: Contrasting thermodynamic selectivity for Ru-CF2H vs F--Os=CFH
[J].
Huang, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Huang, DJ
;
Koren, PR
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Koren, PR
;
Folting, K
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Folting, K
;
Davidson, ER
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Davidson, ER
;
Caulton, KG
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Caulton, KG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(37)
:8916
-8931
←
1
2
3
→