Discovery of Oxygen Induced Chemoselectivity in Pd-Catalyzed C-H Functionalization: Cross-Dehydrogenative Coupling vs C-H Amination

被引：5

作者：

Ann Babu, Sheba ^{[1
,2
]}

Varughese, Sunil ^{[1
,2
]}

Mathew, Jomon ^{[3
]}

John, Jubi ^{[1
,2
]}

机构：

[1] Natl Inst Interdisciplinary Sci & Technol NIIST, Chem Sci & Technol Div, CSIR, Thiruvananthapuram 695019, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] St Josephs Coll Autonomous, Res & Postgrad Dept Chem, Calicut 673008, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 14期

关键词：

AEROBIC OXIDATIVE AMINATION; TRANSIENT DIRECTING GROUPS; MOLECULAR-OXYGEN; BOND FORMATION; ORTHO-OLEFINATION; C(SP(3))-H BONDS; PALLADIUM; ACTIVATION; DERIVATIVES; CARBAZOLES;

D O I：

10.1021/acs.joc.3c00651

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have come across a substrate namely, 5-benzoyl-pyrrolo[2,1-a]isoquinoline in which three different functionalizableC-H bonds were identified that could be judiciously transformedsite selectively for the generation of complex polyring fused N-heterocycles. A Pd-catalyzed cross-dehydrogenative couplingof 5-benzoyl-pyrrolo[2,1-a]isoquinoline afforded8H-indeno-pyrrolo[2,1-a]isoquinolinoneand an oxygen induced palladium catalyzed selective C-H aminationin the same substrate provided a pentacene viz., 9H-indolo-pyrrolo[2,1-a]isoquinoline. We also observedthe formation of a multiring fused benzazepine scaffold by the siteselective C-H amination in 5-(4-nitro benzoyl)-pyrrolo[2,1-a]isoquinoline.

引用

页码：9877 / 9892

页数：16

共 50 条

[21] Non-directed Pd-catalyzed C-H amination of arenes
Bandara, Dhammika
McKeogh, Brenden
Emmert, Marion H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[22] Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds
Correia, Camille A.
Li, Chao-Jun
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) : 1446 - 1450
[23] Ruthenium(II)-catalyzed cross-dehydrogenative C-H alkenylations by triazole assistance
Tirler, Carina
Ackermann, Lutz
TETRAHEDRON, 2015, 71 (26-27) : 4543 - 4551
[24] Pd-Catalyzed C-H Bond Functionalization on the Indole and Pyrrole Nucleus
Beck, Elizabeth M.
Gaunt, Matthew J.
C-H ACTIVATION, 2010, 292 : 85 - 121
[25] Direct Allylic Functionalization Through Pd-Catalyzed C-H Activation
Liron, Frederic
Oble, Julie
Lorion, Melanie M.
Poli, Giovanni
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (27) : 5863 - 5883
[26] Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds†
Capaldo, Luca
Quadri, Lorenzo L.
Merli, Daniele
Ravelli, Davide
CHEMICAL COMMUNICATIONS, 2021, 57 (36) : 4424 - 4427
[27] A walk around the application of nanocatalysts for cross-dehydrogenative coupling of C-H bonds
Wang, Jianjie
Su, Pingyang
Abdolmohammadi, Shahrzad
Vessally, Esmail
RSC ADVANCES, 2019, 9 (71) : 41684 - 41702
[28] Room-temperature C-H arylation by visible-light photocatalysis and Pd-catalyzed C-H functionalization
McMurtrey, Kate B.
Kalyani, Dipannita
Neufeldt, Sharon R.
Sanford, Melanie S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[29] CeO2-Catalyzed C-H Functionalization of N-Aryltetrahydroisoquinolines: An Aerobic Cross-Dehydrogenative Coupling Reaction between Two sp3 C-H Bonds
Sharma, Kumud
Borah, Ashwini
Neog, Kashmiri
Gogoi, Pranjal
CHEMISTRYSELECT, 2016, 1 (15): : 4620 - 4623
[30] Pd-catalyzed, nondirected C-H aminations
Emmert, Marion H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245

← 1 2 3 4 5 →