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Metal-free cross-coupling reactions of aryl sulfonates and phosphates through photoheterolysis of aryl-oxygen bonds
被引:64
作者
:
De Carolis, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
De Carolis, M
[
1
]
Protti, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Protti, S
[
1
]
Fagnoni, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Fagnoni, M
[
1
]
Albini, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Albini, A
[
1
]
机构
:
[1]
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2005年
/ 44卷
/ 08期
关键词
:
arylation;
aryl cations;
aryl esters;
cross-coupling;
photochemistry;
D O I
:
10.1002/anie.200461444
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Photochemical cleavage of Ar-O bonds in phenyl esters substituted with electron-donating groups offers a convenient method for the arylation of alkenes and arenes. The reaction proceeds by an SN1 mechanism via a triplet phenyl cation to form allylbenzene or biphenyl derivatives under mild conditions (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1232 / 1236
页数:5
相关论文
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PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES
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Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Chabaud, L
;
James, P
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0
h-index:
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Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
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Landais, Y
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Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
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PHOTOCHEMISTRY OF IRGASAN-TRIFLATE - A SIMPLE CONVERSION OF AN AROMATIC HYDROXYL GROUP TO CHLORINE IN THE SYNTHESIS OF POLYCHLORINATED DIPHENYL ETHERS AND POLYCHLORINATED DIBENZOFURANS
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CHANG, YS
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OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331
CHANG, YS
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JANG, JS
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OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331
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DEINZER, ML
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OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331
DEINZER, ML
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TETRAHEDRON,
1990,
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PENTAFLUOROPHENYLATION OF AROMATICS WITH PENTAFLUOROPHENYL PERFLUOROALKANESULFONATE AND POLYFLUOROALKANESULFONATE - A PHOTOINDUCED ELECTRON-TRANSFER CATION DIRADICAL COUPLING PROCESS
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CHEN, QY
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Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
CHEN, QY
;
LI, ZT
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Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
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Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
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Dankwardt, JW
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DSM Pharmaceut Chem, Greenville, NC 27834 USA
DSM Pharmaceut Chem, Greenville, NC 27834 USA
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Aromatic allylation via diazotization: Variation of the allylic moiety and a short route to a benzazepine derivative
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Ek, F
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Lund Univ, Dept Chem, S-22100 Lund, Sweden
Ek, F
;
Wistrand, LG
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0
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0
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0
机构:
Lund Univ, Dept Chem, S-22100 Lund, Sweden
Wistrand, LG
;
Frejd, T
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0
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Lund Univ, Dept Chem, S-22100 Lund, Sweden
Frejd, T
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JOURNAL OF ORGANIC CHEMISTRY,
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Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi
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Elhalem, E
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0
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Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
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Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
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Ujváry, I
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Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Ujváry, I
;
Szajnman, SH
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Szajnman, SH
;
Rodriguez, JB
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Rodriguez, JB
.
JOURNAL OF MEDICINAL CHEMISTRY,
2002,
45
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:3984
-3999
[9]
A novel α-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations
[J].
Fraboni, A
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0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Fraboni, A
;
Fagnoni, M
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Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
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Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
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JOURNAL OF ORGANIC CHEMISTRY,
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Freccero, M
;
Fagnoni, M
论文数:
0
引用数:
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Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Fagnoni, M
;
Albini, A
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引用数:
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Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Albini, A
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
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:13182
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←
1
2
3
4
→
共 39 条
[1]
PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES
[J].
BADONE, D
论文数:
0
引用数:
0
h-index:
0
BADONE, D
;
CECCHI, R
论文数:
0
引用数:
0
h-index:
0
CECCHI, R
;
GUZZI, U
论文数:
0
引用数:
0
h-index:
0
GUZZI, U
.
JOURNAL OF ORGANIC CHEMISTRY,
1992,
57
(23)
:6321
-6323
[2]
Bellus D., 1971, ADV PHOTOCHEM, V8, P109, DOI 10.1002/9780470133385.ch3
[3]
Allylsilanes in organic synthesis - Recent developments
[J].
Chabaud, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Chabaud, L
;
James, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
James, P
;
Landais, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France
Landais, Y
.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2004,
2004
(15)
:3173
-3199
[4]
PHOTOCHEMISTRY OF IRGASAN-TRIFLATE - A SIMPLE CONVERSION OF AN AROMATIC HYDROXYL GROUP TO CHLORINE IN THE SYNTHESIS OF POLYCHLORINATED DIPHENYL ETHERS AND POLYCHLORINATED DIBENZOFURANS
[J].
CHANG, YS
论文数:
0
引用数:
0
h-index:
0
机构:
OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331
CHANG, YS
;
JANG, JS
论文数:
0
引用数:
0
h-index:
0
机构:
OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331
JANG, JS
;
DEINZER, ML
论文数:
0
引用数:
0
h-index:
0
机构:
OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331
DEINZER, ML
.
TETRAHEDRON,
1990,
46
(12)
:4161
-4164
[5]
PENTAFLUOROPHENYLATION OF AROMATICS WITH PENTAFLUOROPHENYL PERFLUOROALKANESULFONATE AND POLYFLUOROALKANESULFONATE - A PHOTOINDUCED ELECTRON-TRANSFER CATION DIRADICAL COUPLING PROCESS
[J].
CHEN, QY
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
CHEN, QY
;
LI, ZT
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
LI, ZT
.
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(09)
:2599
-2604
[6]
Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
[J].
Dankwardt, JW
论文数:
0
引用数:
0
h-index:
0
机构:
DSM Pharmaceut Chem, Greenville, NC 27834 USA
DSM Pharmaceut Chem, Greenville, NC 27834 USA
Dankwardt, JW
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004,
43
(18)
:2428
-2432
[7]
Aromatic allylation via diazotization: Variation of the allylic moiety and a short route to a benzazepine derivative
[J].
Ek, F
论文数:
0
引用数:
0
h-index:
0
机构:
Lund Univ, Dept Chem, S-22100 Lund, Sweden
Ek, F
;
Wistrand, LG
论文数:
0
引用数:
0
h-index:
0
机构:
Lund Univ, Dept Chem, S-22100 Lund, Sweden
Wistrand, LG
;
Frejd, T
论文数:
0
引用数:
0
h-index:
0
机构:
Lund Univ, Dept Chem, S-22100 Lund, Sweden
Frejd, T
.
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(05)
:1911
-1918
[8]
Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi
[J].
Elhalem, E
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Elhalem, E
;
Bailey, BN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Bailey, BN
;
Docampo, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Docampo, R
;
Ujváry, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Ujváry, I
;
Szajnman, SH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Szajnman, SH
;
Rodriguez, JB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina
Rodriguez, JB
.
JOURNAL OF MEDICINAL CHEMISTRY,
2002,
45
(18)
:3984
-3999
[9]
A novel α-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations
[J].
Fraboni, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Fraboni, A
;
Fagnoni, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Fagnoni, M
;
Albini, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Albini, A
.
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(12)
:4886
-4893
[10]
Homolytic vs heterolytic paths in the photochemistry of haloanilines
[J].
论文数:
引用数:
h-index:
机构:
Freccero, M
;
Fagnoni, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Fagnoni, M
;
Albini, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Albini, A
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(43)
:13182
-13190
←
1
2
3
4
→