共 38 条
Oxidative coupling of arylboronic acids with arenes via Rh-catalyzed direct C-H arylation
被引:150
作者:

Vogler, Thomas
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munster, Inst Organ Chem, Fachbereich Chem, D-48149 Munster, Germany Univ Munster, Inst Organ Chem, Fachbereich Chem, D-48149 Munster, Germany

Studer, Armido
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munster, Inst Organ Chem, Fachbereich Chem, D-48149 Munster, Germany Univ Munster, Inst Organ Chem, Fachbereich Chem, D-48149 Munster, Germany
机构:
[1] Univ Munster, Inst Organ Chem, Fachbereich Chem, D-48149 Munster, Germany
关键词:
D O I:
10.1021/ol702659a
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Oxidative coupling of three different arenes and a thiophene derivative with various arylboronic acids was achieved with a [RhCl(C2H4)(2)](2)/ P[p-(CF3)C6H4](3) catalyst system. Commercially available 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) was used as a stoichiometric oxidant. A 2-pyridyl group and an imine functional group served as ortho-directing groups to mediate the direct C-H arylation by a Rh complex. Moderate to excellent yields were obtained for the coupling reactions.
引用
收藏
页码:129 / 131
页数:3
相关论文
共 38 条
[1]
Catalytic arylation reactions by C-H bond activation with aryl tosylates
[J].
Ackermann, L
;
Althammer, A
;
Born, R
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006, 45 (16)
:2619-2622

Ackermann, L
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

Althammer, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

Born, R
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
[2]
Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides
[J].
Ackermann, L
.
ORGANIC LETTERS,
2005, 7 (14)
:3123-3125

Ackermann, L
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
[3]
Ruthenium(IV) alkylidenes as precatalysts for direct arylations of Alkenes with aryl chlorides and an application to sequential catalysis
[J].
Ackermann, Lutz
;
Born, Robert
;
Alvarez-Bercedo, Paula
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2007, 46 (33)
:6364-6367

Ackermann, Lutz
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

Born, Robert
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

Alvarez-Bercedo, Paula
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[4]
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
[J].
Alberico, Dino
;
Scott, Mark E.
;
Lautens, Mark
.
CHEMICAL REVIEWS,
2007, 107 (01)
:174-238

Alberico, Dino
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada

Scott, Mark E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada

Lautens, Mark
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
[5]
(ETA-6-BENZENE)(ETA-5-ETHYLTETRAMETHYLCYCLOPENTADIENYL)RHODIUM (III) HEXAFLUOROPHOSPHATE - A REAGENT FOR CATALYTIC PHENOL OXIDATIVE COUPLING
[J].
BARRETT, AGM
;
ITOH, T
;
WALLACE, EM
.
TETRAHEDRON LETTERS,
1993, 34 (14)
:2233-2234

BARRETT, AGM
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Colorado State University Fort Collins

ITOH, T
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Colorado State University Fort Collins

WALLACE, EM
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Colorado State University Fort Collins
[6]
The catalytic intermolecular orthoarylation of phenols
[J].
Bedford, RB
;
Coles, SJ
;
Hursthouse, MB
;
Limmert, ME
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003, 42 (01)
:112-114

Bedford, RB
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

Coles, SJ
论文数: 0 引用数: 0
h-index: 0
机构: Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

Hursthouse, MB
论文数: 0 引用数: 0
h-index: 0
机构: Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

Limmert, ME
论文数: 0 引用数: 0
h-index: 0
机构: Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
[7]
Atroposelective synthesis of axially chiral biaryl compounds
[J].
Bringmann, G
;
Mortimer, AJP
;
Keller, PA
;
Gresser, MJ
;
Garner, J
;
Breuning, M
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005, 44 (34)
:5384-5427

Bringmann, G
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

Mortimer, AJP
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

Keller, PA
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

Gresser, MJ
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

Garner, J
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

Breuning, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[8]
SYNTHESES OF RHODIUM AND IRIDIUM (OCTAETHYLPORPHYRINATO)METAL DIMERS FROM TEMPO
[J].
CHAN, KS
;
LEUNG, YB
.
INORGANIC CHEMISTRY,
1994, 33 (14)
:3187-3187

CHAN, KS
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637 UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637

LEUNG, YB
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637 UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
[9]
Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways
[J].
Chen, Xiao
;
Goodhue, Charles E.
;
Yu, Jin-Quan
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006, 128 (39)
:12634-12635

Chen, Xiao
论文数: 0 引用数: 0
h-index: 0
机构:
Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA

Goodhue, Charles E.
论文数: 0 引用数: 0
h-index: 0
机构:
Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA

Yu, Jin-Quan
论文数: 0 引用数: 0
h-index: 0
机构:
Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA
[10]
Room temperature palladium-catalyzed 2-arylation of indoles
[J].
Deprez, NR
;
Kalyani, D
;
Krause, A
;
Sanford, MS
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006, 128 (15)
:4972-4973

Deprez, NR
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Kalyani, D
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Krause, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Sanford, MS
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA