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Literature DB >> 15846437

Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters.

David N Coventry¹, Andrei S Batsanov, Andres E Goeta, Judith A K Howard, Todd B Marder, Robin N Perutz.

Abstract

The selectivity of the iridium boryl complex-catalysed reaction of pyrene and perylene with B2(pin)2 (pin = OCMe2CMe2O) has been employed in the synthesis of D(2h)-symmetry pyrene-2,7-(Bpin)2 and D(4h)-symmetry perylene-2,5,8,11-(Bpin)4 providing direct borylation of positions which are otherwise difficult to derivatise.

Entities: Chemical Species

Year: 2005 PMID： 15846437 DOI： 10.1039/b501778e

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

20 in total

1. Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors: Bo Su; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2018-07-13 Impact factor: 15.336

2. Palladium catalysed C-H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions.

Authors: Xavier Just-Baringo; Yuyoung Shin; Adyasha Panigrahi; Marco Zarattini; Vaiva Nagyte; Ling Zhao; Kostas Kostarelos; Cinzia Casiraghi; Igor Larrosa
Journal: Chem Sci Date: 2020-01-28 Impact factor: 9.825

3. 1,3-Dimethyl 5-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxyl-ate.

Authors: Long-Tao Yi; Zhi-Qiang Liu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-01-07

4. 4,4,5,5-Tetra-methyl-2-[1,3,6,8-tetra-bromo-7-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane.

Authors: Ying Chen; Wen-Tao Yu; Zhi-Qiang Liu; Ping Yu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-02-17

Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters.

1. Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

2. Palladium catalysed C-H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions.

3. 1,3-Dimethyl 5-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxyl-ate.

4. 4,4,5,5-Tetra-methyl-2-[1,3,6,8-tetra-bromo-7-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane.

5. Anomalous coarsening driven by reversible charge transfer at metal-organic interfaces.

6. Cyclophane with eclipsed pyrene units enables construction of spin interfaces with chemical accuracy.

7. Boron-rich benzene and pyrene derivatives for the detection of thermal neutrons.

8. Blending gelators to tune gel structure and probe anion-induced disassembly.

Review 9. Transition metal catalyzed borylation of functional π-systems.

10. Formation of C(sp(2))-boronate esters by borylative cyclization of alkynes using BCl3.