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Heck coupling with nonactivated alkenyl tosylates and phosphates: Examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates
被引:166
作者
:
Hansen, Anders L.
论文数:
0
引用数:
0
h-index:
0
机构:
Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
Hansen, Anders L.
Ebran, Jean-Philippe
论文数:
0
引用数:
0
h-index:
0
机构:
Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
Ebran, Jean-Philippe
Ahlquist, Marten
论文数:
0
引用数:
0
h-index:
0
机构:
Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
Ahlquist, Marten
Norrby, Per-Ola
论文数:
0
引用数:
0
h-index:
0
机构:
Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
Norrby, Per-Ola
Skrydstrup, Troels
论文数:
0
引用数:
0
h-index:
0
机构:
Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
Skrydstrup, Troels
机构
:
[1]
Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
[2]
Univ Aarhus, inSPIN, Ctr Insoluble Prot Struct, Dept Chem, DK-8000 Aarhus, Denmark
[3]
Univ Aarhus, Nanosci Ctr, DK-8000 Aarhus, Denmark
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2006年
/ 45卷
/ 20期
关键词
:
1,2-migration;
alkenes;
Heck reaction;
phosphates;
tosylates;
D O I
:
10.1002/anie.200600442
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron-deficient olefins. An unexpected 1,2-migration of the alkenyl Pd II intermediates (see Scheme) leads to the isomerized Heck coupling product. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3349 / 3353
页数:5
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ORGANOMETALLICS,
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DIPEPTIDE ISOSTERES .2. SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERE DIASTEREOMERS FROM A COMMON GAMMA-LACTONE INTERMEDIATE - PREPARATION OF RENIN AND HIV-1 PROTEASE INHIBITOR TRANSITION-STATE MIMICS
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Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
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Steinhuebel, D
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Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
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Synthesis of 3-substituted-4H-1,4-benzoxazines via palladium-catalysed coupling reactions
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Total synthesis of (±)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides
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[8]
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[9]
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Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Fu, XY
Zhang, SY
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Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Zhang, SY
Yin, JG
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[J].
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2003,
42
(48)
: 5993
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5996
←
1
2
3
4
5
→
共 43 条
[1]
Theoretical evidence for low-ligated palladium(0): [Pd-L] as the active species in oxidative addition reactions
Ahlquist, M
论文数:
0
引用数:
0
h-index:
0
机构:
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Ahlquist, M
Fristrup, P
论文数:
0
引用数:
0
h-index:
0
机构:
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Fristrup, P
Tanner, D
论文数:
0
引用数:
0
h-index:
0
机构:
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Tanner, D
Norrby, PO
论文数:
0
引用数:
0
h-index:
0
机构:
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Tech Univ Denmark, Dept Chem, DK-2800 Lyngby KGS, Denmark
Norrby, PO
[J].
ORGANOMETALLICS,
2006,
25
(08)
: 2066
-
2073
[2]
DIPEPTIDE ISOSTERES .2. SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERE DIASTEREOMERS FROM A COMMON GAMMA-LACTONE INTERMEDIATE - PREPARATION OF RENIN AND HIV-1 PROTEASE INHIBITOR TRANSITION-STATE MIMICS
BAKER, WR
论文数:
0
引用数:
0
h-index:
0
机构:
Pharmaceutical Products Division, Abbott Laboratories, Abbott Park
BAKER, WR
PRATT, JK
论文数:
0
引用数:
0
h-index:
0
机构:
Pharmaceutical Products Division, Abbott Laboratories, Abbott Park
PRATT, JK
[J].
TETRAHEDRON,
1993,
49
(39)
: 8739
-
8756
[3]
CYCLOREVERSIONS OF ANIONS FROM TETRAHYDROFURANS - CONVENIENT SYNTHESIS OF LITHIUM ENOLATES OF ALDEHYDES
BATES, RB
论文数:
0
引用数:
0
h-index:
0
BATES, RB
POTTER, DE
论文数:
0
引用数:
0
h-index:
0
POTTER, DE
KROPOSKI, LM
论文数:
0
引用数:
0
h-index:
0
KROPOSKI, LM
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1972,
37
(04)
: 560
-
&
[4]
Stereoselective enol tosylation:: Preparation of trisubstituted α,β-unsaturated esters
Baxter, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Baxter, JM
Steinhuebel, D
论文数:
0
引用数:
0
h-index:
0
机构:
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Steinhuebel, D
Palucki, M
论文数:
0
引用数:
0
h-index:
0
机构:
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Palucki, M
Davies, IW
论文数:
0
引用数:
0
h-index:
0
机构:
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
Davies, IW
[J].
ORGANIC LETTERS,
2005,
7
(02)
: 215
-
218
[5]
Synthesis of 3-substituted-4H-1,4-benzoxazines via palladium-catalysed coupling reactions
Buon, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
Buon, C
Bouyssou, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
Bouyssou, P
Coudert, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
Coudert, G
[J].
TETRAHEDRON LETTERS,
1999,
40
(04)
: 701
-
702
[6]
Total synthesis of (±)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides
Coe, JW
论文数:
0
引用数:
0
h-index:
0
机构:
Pfizer Inc, Pfizer Global Res & Dev, Groton, CT 06340 USA
Pfizer Inc, Pfizer Global Res & Dev, Groton, CT 06340 USA
Coe, JW
[J].
ORGANIC LETTERS,
2000,
2
(26)
: 4205
-
4208
[7]
De Meijere A., 2004, Metal-Catalyzed Cross-Coupling Reactions
[8]
FRYDMAN N, 1969, J CHEM SOC CHEM COMM, P1044
[9]
First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction
Fu, XY
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Fu, XY
Zhang, SY
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Zhang, SY
Yin, JG
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Yin, JG
McAllister, TL
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
McAllister, TL
Jiang, SA
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Jiang, SA
Tann, CH
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Tann, CH
Thiruvengadam, TK
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Thiruvengadam, TK
Zhang, FC
论文数:
0
引用数:
0
h-index:
0
机构:
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Schering Plough Res Inst, Dept Synthet Chem, Union, NJ 07083 USA
Zhang, FC
[J].
TETRAHEDRON LETTERS,
2002,
43
(04)
: 573
-
576
[10]
Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: Use of a copper cocatalyst inhibits the reaction
Gelman, D
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Gelman, D
Buchwald, SL
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Buchwald, SL
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003,
42
(48)
: 5993
-
5996
←
1
2
3
4
5
→