Annulative π-Extension by Cp*Co(III)-Catalyzed Ketone-Directed peri-Annulation: An Approach to Access Fused Arenes

被引：0

作者：

Bhattacharyya, Arya ^{[1
]}

Sk, Md Raja ^{[1
]}

Sen, Supreeta ^{[1
]}

Kundu, Samrat ^{[1
]}

Maji, Modhu Sudan ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 48期

关键词：

AROMATIC-HYDROCARBON; GRAPHENE NANORIBBONS; RAPID ACCESS; BAY REGIONS; FUNCTIONALIZATION; PYRENES;

D O I：

10.1021/acs.orglett.3c03443

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A masked-bay-region selective first-row transition-metal Cp*Co(III)-catalyzed annulative pi-extension of arene-derived ketones is achieved to afford K-region-functionalized benzo[e]pyrenes, benzotetraphenes, and pyrenes. Comprehensive density functional theory studies buttress the mechanistic pathway comprising key steps like peri-C-H activation, alkyne 1,2-migratory insertion, and nucleophilic attack toward ketone, this attack being the rate-determining step. In addition, pi-conjugated 1,1 '-bipyrenes, potential photocatalyst pyrene-quinones, and putative n-type semiconductor cyano group-containing dibenzo[de,qr]tetracenes are also accessed.

引用

页码：8622 / 8627

页数：6

共 9 条

[1] Weakly Coordinating, Ketone-Directed Cp*Co(III)-Catalyzed C-H Allylation on Arenes and Indoles
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ORGANIC LETTERS, 2018, 20 (01) : 134 - 137
[2] Annulative π-Extension by Rhodium(III)-Catalyzed Ketone-Directed C-H Activation: Rapid Access to Pyrenes and Related Polycyclic Aromatic Hydrocarbons (PAHs)
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[3] Cp*Co(III)-Catalyzed Ketone-Directed ortho-C-H Activation for the Synthesis of Indene Derivatives
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[6] Weakly coordinating, ketone-directed cobalt(III)-catalyzed C-H allylation, alkenylation, and vinylation: Easy access to the simple and useful structural motifs
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[7] Cp*Co(iii)-catalyzed thiocarbamate-directed C-H aminocarbonylation, amination, and cascade annulation of pyrroles
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[8] (Benz)Imidazole-Directed Cobalt(III)-Catalyzed C-H Activation of Arenes: A Facile Strategy to Access Polyheteroarenes by Oxidative Annulation
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[9] Thiocarbamate-directed Cp*Co(III)-Catalyzed Olefinic C-H Amidation: Facile Access to Enamines with High (Z)-Selectivity
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