共 44 条
Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers
被引:13
作者:

Basnet, Prakash
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

Sebold, Melissa B.
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h-index: 0
机构:
Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

Hendrick, Charles E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

Kozlowski, Marisa C.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
机构:
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
关键词:
C-H BONDS;
CHEMOSELECTIVE ACTIVATION;
QUATERNARY STEREOCENTERS;
IMINONITRILES;
DIMERS;
SP(3);
D O I:
10.1021/acs.orglett.0c03581
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
We describe herein a Cu(OTf)(2) catalyzed oxidative arylation of a tertiary carbon-containing substrate including aryl malononitriles, 3-aryl benzofuran-2-ones, and 3-aryl oxindoles. In some cases, the nitrile groups of the aryl malononitriles undergo further reactions leading to lactones or imines. These reaction conditions are applicable for a range of arenes, including phenols, anilines, anisoles, and heteroarenes. Mechanistic studies support the formation of a cationic intermediate via a two-electron oxidation.
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页码:9524 / 9528
页数:5
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共 44 条
[1]
THE KINETICS OF THE DECOMPOSITION OF POTASSIUM PERSULFATE IN AQUEOUS SOLUTIONS OF METHANOL
[J].
BARTLETT, PD
;
COTMAN, JD
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1949, 71 (04)
:1419-1422

BARTLETT, PD
论文数: 0 引用数: 0
h-index: 0

COTMAN, JD
论文数: 0 引用数: 0
h-index: 0
[2]
An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers
[J].
Bogle, Katherine M.
;
Hirst, David J.
;
Dixon, Darren J.
.
ORGANIC LETTERS,
2007, 9 (23)
:4901-4904

Bogle, Katherine M.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

Hirst, David J.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[3]
An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine
[J].
Bogle, Katherine M.
;
Hirst, David J.
;
Dixon, Darren J.
.
TETRAHEDRON,
2010, 66 (33)
:6399-6410

Bogle, Katherine M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Hirst, David J.
论文数: 0 引用数: 0
h-index: 0
机构:
GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
[4]
Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms
[J].
Bueschleb, Martin
;
Dorich, Stephane
;
Hanessian, Stephen
;
Tao, Daniel
;
Schenthal, Kyle B.
;
Overman, Larry E.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2016, 55 (13)
:4156-4186

Bueschleb, Martin
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada

Dorich, Stephane
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada

Hanessian, Stephen
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada

Tao, Daniel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, 1102 Nat Sci 2, Irvine, CA 92697 USA Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada

Schenthal, Kyle B.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, 1102 Nat Sci 2, Irvine, CA 92697 USA Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada

Overman, Larry E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, 1102 Nat Sci 2, Irvine, CA 92697 USA Univ Montreal, Dept Chem, Stn Ctr Ville CP 6128, Montreal, PQ H3C 3J7, Canada
[5]
Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus
[J].
Cui, CB
;
Kakeya, H
;
Osada, H
.
JOURNAL OF ANTIBIOTICS,
1996, 49 (08)
:832-835

Cui, CB
论文数: 0 引用数: 0
h-index: 0
机构:
RIKEN, INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN RIKEN, INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN

Kakeya, H
论文数: 0 引用数: 0
h-index: 0
机构:
RIKEN, INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN RIKEN, INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN

Osada, H
论文数: 0 引用数: 0
h-index: 0
机构:
RIKEN, INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN RIKEN, INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN
[6]
Chemoselective Activation of sp3 vs sp2 C-H Bonds with Pd(II)
[J].
Curto, John M.
;
Kozlowski, Marisa C.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2015, 137 (01)
:18-21

Curto, John M.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

Kozlowski, Marisa C.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Penn, Dept Chem, Philadelphia, PA 19104 USA Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
[7]
OXIDATIVE CARBON-CARBON COUPLING .1. OXIDATIVE COUPLING OF ALPHA-SUBSTITUTED BENZYL CYANIDES
[J].
DEJONGH, HAP
;
DEJONGE, CRH
;
MIJS, WJ
.
JOURNAL OF ORGANIC CHEMISTRY,
1971, 36 (21)
:3160-&

DEJONGH, HAP
论文数: 0 引用数: 0
h-index: 0

DEJONGE, CRH
论文数: 0 引用数: 0
h-index: 0

MIJS, WJ
论文数: 0 引用数: 0
h-index: 0
[8]
Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore
[J].
Fleming, Fraser F.
;
Yao, Lihua
;
Ravikumar, P. C.
;
Funk, Lee
;
Shook, Brian C.
.
JOURNAL OF MEDICINAL CHEMISTRY,
2010, 53 (22)
:7902-7917

Fleming, Fraser F.
论文数: 0 引用数: 0
h-index: 0
机构:
Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA

Yao, Lihua
论文数: 0 引用数: 0
h-index: 0
机构:
Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA

Ravikumar, P. C.
论文数: 0 引用数: 0
h-index: 0
机构:
Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA

Funk, Lee
论文数: 0 引用数: 0
h-index: 0
机构:
Mylan Pharmaceut Inc, Morgantown, WV 26505 USA Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA

Shook, Brian C.
论文数: 0 引用数: 0
h-index: 0
机构:
Johnson & Johnson Pharmaceut Res & Dev LLC, Spring House, PA 19477 USA Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA
[9]
One-pot three-component synthesis of α-iminonitriles by IBX/TBAB-Mediated oxidative Strecker reaction
[J].
Fontaine, Patrice
;
Chiaroni, Angele
;
Masson, Geraldine
;
Zhu, Jieping
.
ORGANIC LETTERS,
2008, 10 (08)
:1509-1512

Fontaine, Patrice
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

Chiaroni, Angele
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

Masson, Geraldine
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

Zhu, Jieping
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[10]
Bond dissociation energies for radical dimers derived from highly stabilized carbon-centered radicals
[J].
Frenette, M
;
Aliaga, C
;
Font-Sanchis, E
;
Scaiano, JC
.
ORGANIC LETTERS,
2004, 6 (15)
:2579-2582

Frenette, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

Aliaga, C
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

论文数: 引用数:
h-index:
机构:

Scaiano, JC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada