Nickel-Catalyzed C(sp2)-H/C(sp3)-H Oxidative Coupling of Indoles with Toluene Derivatives

被引：75

作者：

Soni, Vineeta ^{[1
]}

Khake, Shrikant M. ^{[1
]}

Punji, Benudhar ^{[1
]}

机构：

[1] Natl Chem Lab, CSIR, Organometall Synth & Catalysis Grp, Chem Engn Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

来源：

ACS CATALYSIS | 2017年 / 7卷 / 06期

关键词：

benzylation; C-H activation; indoles; nickel; oxidative coupling; pincer complex; C-H BOND; UNACTIVATED C(SP(3))-H BONDS; CARBON-HYDROGEN BONDS; CHELATION ASSISTANCE; DIRECT ALKYLATION; NATURAL-PRODUCTS; DIRECTING GROUPS; DIRECT ARYLATION; ARYL HALIDES; ACTIVATION;

D O I：

10.1021/acscatal.7b01044

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Nickel-catalyzed oxidative C(sp(2))-H/C(sp(3))-H coupling of indoles with toluene derivatives is successfully achieved in the presence of 2-iodobutane as the oxidant. This method allows the selective C-2 benzylation of indoles with toluene derivatives over the alkylation with 2-iodobutane and permits the coupling of diversified indoles via the monochelation assistance. The reaction proceeded through a single-electron-transfer (SET) process, wherein both the C-H nickelation of indole and the C-H activation of toluene derivatives have a significant effect on the entire reaction rate. The synthetic utility of this nickel-catalyzed protocol is demonstrated by the facile removal of the directing group and by the convenient synthesis of the melatonin receptor antagonist Luzindole derivatives.

引用

页码：4202 / 4208

页数：7

共 99 条

[1] Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes
Ackermann, Lutz
Lygin, Alexander V.
[J]. ORGANIC LETTERS, 2011, 13 (13) : 3332 - 3335
[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[3] The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group
Aihara, Yoshinori
Wuelbern, Jendrik
Chatani, Naoto
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) : 438 - 446
[4] Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives
Aihara, Yoshinori
Tobisu, Mamoru
Fukumoto, Yoshiya
Chatani, Naoto
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) : 15509 - 15512
[5] Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance
Aihara, Yoshinori
Chatani, Naoto
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5308 - 5311
[6] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[7] Toward the Definition of Stereochemical Requirements for MT2-Selective Antagonists and Partial Agonists by Studying 4-Phenyl-2-propionamidotetralin Derivatives
Bedini, Annalida
Lucarini, Simone
Spadoni, Gilberto
Tarzia, Giorgio
Scaglione, Francesco
Dugnani, Silvana
Pannacci, Marilou
Lucini, Valeria
Carmi, Caterina
Pala, Daniele
Rivara, Silvia
Mor, Marco
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (24) : 8362 - 8372
[8] Synthesis of novel PPARα/γ dual agonists as potential drugs for the treatment of the metabolic syndrome and diabetes type II designed using a new de novo design program PROTOBUILD
Bhurruth-Alcor, Yushma
Rost, Therese
Jorgensen, Michael R.
Kontogiorgis, Christos
Skorve, Jon
Cooper, Robert G.
Sheridan, Joseph M.
Hamilton, William D. O.
Heal, Jonathan R.
Berge, Rolf K.
Miller, Andrew D.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) : 1169 - 1188
[9] Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T
Bhuyan, Ranjana
Nicholas, Kenneth M.
[J]. ORGANIC LETTERS, 2007, 9 (20) : 3957 - 3959
[10] Au-Catalyzed Cross-Coupling of Arenes via Double C-H Activation
Cambeiro, Xacobe C.
Ahlsten, Nanna
Larrosa, Igor
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) : 15636 - 15639

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