Rhodium(III)-Catalysed Carbenoid C(sp2)-H Functionalisation of Aniline Substrates with α-Diazo Esters: Formation of Oxindoles and Characterisation/Utility of an Intermediate-Like Rhodacycle

被引：31

作者：

Allu, Srinivasarao ^{[1
]}

Ravi, Manjula ^{[1
]}

Swamy, K. C. Kumara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 34期

关键词：

C-H activation; Rhodium; Homogeneous catalysis; Nucleobases; Nitrogen heterocycles; Nucleosides; C-H ACTIVATION; REVERSE-TRANSCRIPTASE INHIBITORS; BOND FUNCTIONALIZATION; DIRECTING GROUP; METAL CARBENE; RH(III)-CATALYZED SYNTHESIS; N-OXIDES; BIOLOGICAL EVALUATIONS; FACILE SYNTHESIS; DERIVATIVES;

D O I：

10.1002/ejoc.201600968

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Rh-III-catalysed reaction of 2-anilinopyridines with sulfonylated alpha-diazo esters under mild conditions gave oxindole derivatives, while an analogous reaction of anilinopyrimidine precursors using alpha-diazo esters led to the ortho- alkylation products. The carbenoid coupling reaction was successfully extended to 6-anilinopurine/purine nucleosides, and the ortho-alkylated 6-anilinopurines could be obtained in excellent yields. Proof of the involvement of an Rh-C-bonded species comes from the characterisation of an intermediate-like rhodacycle (which is also an active catalyst) by single-crystal X-ray crystallography.

引用

页码：5697 / 5705

页数：9

共 6 条

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Panpan Tian
Chao Feng
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Feng, Chao
Loh, Teck-Peng
NATURE COMMUNICATIONS, 2015, 6
[3] Rhodium(III)-catalysed, redox-neutral C(sp2)-H alkenylation using pivalimide as a directing group with internal alkynes
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TETRAHEDRON LETTERS, 2017, 58 (01) : 1 - 4
[4] Synthesis of Naphthoquinolizinones through Rh(III)-Catalyzed Double C(sp2)-H Bond Carbenoid Insertion and Annulation of 2-Aryl-3-cyanopyridines with α-Diazo Carbonyl Compounds
Zhang, Beibei
Li, Bin
Zhang, Xin-Ying
Fan, Xuesen
ORGANIC LETTERS, 2017, 19 (09) : 2294 - 2297
[5] C(SP3)-H AND C(SP2)-H BOND ACTIVATION IN THE (PENTAMETHYLCYCLOPENTADIENYL)RHODIUM(III) SYSTEM - FORMATION OF (2,2-DIMETHYLPROPANE-1,3-DIYL)(PENTAMETHYLCYCLOPENTADIENYL)(TRIPHENYLPHOSPHINE)RHODIUM AND NEOPENTYL(PENTAMETHYLCYCLOPENTADIENYL)(TRIPHENYLPHOSPHINE-C2,P)-RHODIUM
DIVERSI, P
INGROSSO, G
LUCHERINI, A
FASCE, D
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (16) : 945 - 946
[6] Highly regioselective rhodium(II)-catalysed carbenoid insertion reaction into sp2 C-H bond:: a general method for the synthesis of 3,3a-dihydro-2H,5H-pyrrolo[1,2-a]quinoline-1,4-dione ring system
Haldar, P
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Ray, JK
TETRAHEDRON LETTERS, 2003, 44 (40) : 7433 - 7435

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