Intermolecular chemo- and regioselective aromatic C-H amination of alkoxyarenes promoted by rhodium nitrenoids

被引：19

作者：

Arai, Kenta ^{[1
]}

Ueda, Yoshihiro ^{[1
]}

Morisaki, Kazuhiro ^{[1
]}

Furuta, Takumi ^{[1
]}

Sasamori, Takahiro ^{[2
]}

Tokitoh, Norihiro ^{[1
]}

Kawabata, Takeo ^{[1
]}

机构：

[1] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan

[2] Nagoya City Univ, Grad Sch Nat Sci, Mizuho Ku, Yamanohata 1,Mizuho Cho, Nagoya, Aichi 4678501, Japan

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 18期

关键词：

RH-CATALYZED AMINATION; FUNCTIONAL MOLECULES; PHOTOREDOX CATALYSIS; ORIENTED AROMATICS; BONDS; IMIDATION; INSERTIONS; OXIDATION; AMINES; OXAZOLIDINONES;

D O I：

10.1039/c7cc09952e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Intermolecular aromatic C(sp(2))-H amination promoted by neutral rhodium nitrenoids has been developed. The reactions proceeded with various oxygen-substituted arenes (1.5 equiv.) in a chemo- and regioselective manner. The aromatic C(sp(2))-H amination took place at the para position of the oxygen substituent in the presence of benzylic C(sp(3))-H bonds and/or C(sp(3))-H bonds to ethereal oxygen.

引用

页码：2264 / 2267

页数：4

共 58 条

[1] Boursalian GB, 2016, NAT CHEM, V8, P810, DOI [10.1038/nchem.2529, 10.1038/NCHEM.2529]
[2] Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent
Boursalian, Gregory B.
Ngai, Ming-Yu
Hojczyk, Katarzyna N.
Ritter, Tobias
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) : 13278 - 13281
[3] INTRAMOLECULAR NITRENE C-H INSERTIONS MEDIATED BY TRANSITION-METAL COMPLEXES AS NITROGEN ANALOGS OF CYTOCHROME-P-450 REACTIONS
BRESLOW, R
GELLMAN, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) : 6728 - 6729
[4] Dirhodium(II)-Catalyzed C(sp3)-H Amination Using Iodine(III) Oxidants
Buendia, Julien
Grelier, Gwendal
Dauban, Philippe
[J]. ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 64, 2015, 64 : 77 - 118
[5] Transition metal-catalyzed iodine(III)-mediated nitrene transfer reactions: efficient tools for challenging syntheses
Darses, B.
Rodrigues, R.
Neuville, L.
Mazurais, M.
Dauban, P.
[J]. CHEMICAL COMMUNICATIONS, 2017, 53 (03) : 493 - 508
[6] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion
Davies, Huw M. L.
Manning, James R.
[J]. NATURE, 2008, 451 (7177) : 417 - 424
[7] Diamond D, 1996, CHEM SOC REV, V25, P15, DOI 10.1039/cs9962500015
[8] Expanding the scope of C-H amination through catalyst design
Espino, CG
Fiori, KW
Kim, M
Du Bois, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) : 15378 - 15379
[9] Espino CG, 2001, ANGEW CHEM INT EDIT, V40, P598, DOI 10.1002/1521-3773(20010202)40:3<598::AID-ANIE598>3.0.CO
[10] 2-9

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