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
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
收藏
页码:9877 / 9892
页数:16
相关论文
共 99 条
[1]   SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].
ARNDTSEN, BA ;
BERGMAN, RG ;
MOBLEY, TA ;
PETERSON, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162
[2]  
Babu SA, 2022, chemRxiv, DOI [10.26434/chemrxiv-2022-2pl58, 10.26434/chemrxiv-2022-2pl58, DOI 10.26434/CHEMRXIV-2022-2PL58]
[3]   Unprecedented access to functionalized pyrrolo[2,1-a]isoquinolines from the domino reaction of isoquinolinium ylides and electrophilic benzannulated heterocycles [J].
Babu, Sheba Ann ;
Rajalekshmi, A. R. ;
Nitha, P. R. ;
Omanakuttan, Vishnu K. ;
Rahul, P. ;
Varughese, Sunil ;
John, Jubi .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (08) :1807-1817
[4]   Recent Developments in Transition Metal-Free Cross-Dehydrogenative Coupling Reactions for C-C Bond Formation [J].
Batra, Aanchal ;
Singh, Kamal Nain .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (43) :6676-6703
[5]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[6]   A highly site-selective radical sp3 C-H amination of azaheterocycles [J].
Bentley, Keith W. ;
Dummit, Krysta A. ;
Van Humbeck, Jeffrey F. .
CHEMICAL SCIENCE, 2018, 9 (30) :6440-6445
[7]   Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].
Berger, Florian ;
Plutschack, Matthew B. ;
Riegger, Julian ;
Yu, Wanwan ;
Speicher, Samira ;
Ho, Matthew ;
Frank, Nils ;
Ritter, Tobias .
NATURE, 2019, 567 (7747) :223-228
[8]   Combining transition metals and transient directing groups for C-H functionalizations [J].
Bhattacharya, Trisha ;
Pimparkar, Sandeep ;
Maiti, Debabrata .
RSC ADVANCES, 2018, 8 (35) :19456-19464
[9]   Aerobic oxidative amination of unactivated alkenes catalyzed by palladium [J].
Brice, JL ;
Harang, JE ;
Timokhin, VI ;
Anastasi, NR ;
Stahl, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :2868-2869
[10]   Synthesis of fluoren-9-ones via palladium-catalyzed cyclocarbonylation of o-halobiaryls [J].
Campo, MA ;
Larock, RC .
ORGANIC LETTERS, 2000, 2 (23) :3675-3677