Recent Progress in Iridium-Catalyzed Remote Regioselective C—H Borylation of (Hetero)Arenes

doi:10.6023/cjoc202103020

Abstract

(Hetero)Aryl boronic acids and their derivatives have been widely used in synthetic chemistry, material sciences, and drug discovery. Accordingly, the development of novel synthetic methods towards these structures has received a great deal of attention. In particular, Ir-catalyzed C—H borylation represents one of the most efficient methods. Due to the restriction of the reaction mechanism, regioselective controllable C—H borylation of Ir catalysis is a formidable challenge, and it is also an important development direction in this area. In this review, the recent progress in Ir-catalyzed remote selective C—H borylation of arenes is systematically discussed.

Key words: C—H activation, (hetero)aryl boronates, synthetic methods, borylation

Cite this article

Xiaoliang Zou, Senmiao Xu. Recent Progress in Iridium-Catalyzed Remote Regioselective C—H Borylation of (Hetero)Arenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2610-2620.

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Fig. & Tab. 14

Scheme 1. Ir-catalyzed C—H borylation of arenes and its mechanism

Scheme 2. Hydrogen-bond directed meta-selective C—H borylation

Scheme 3. B—N bond directed formal meta-selective C—H borylation

Scheme 4. Non-covalent interaction directed para-selective C—H borylation of (hetero)aromatic esters

Scheme 5. Ion-pair directed meta-selective C—H borylation of aromatic quaternary ammonium salts

Scheme 6. Ion-pair directed meta-selective C—H borylation of aromatic phosphonium salts

Scheme 7. Hydrogen-bond directed meta-selective C—H borylation

Scheme 8. Hydrogen-bond directed enantioselective meta-selective C—H borylation

Scheme 9. Steric repulsion directed para-selective C—H borylation

Scheme 10. Steric repulsion induced para-selective C—H borylation

Scheme 11. para-Selective C—H borylation by cooperative iridium/aluminum catalysis

Scheme 12. C4-selective C—H borylation of pyridines by cooperative iridium/aluminum catalysis

Scheme 13. meta-Selective C—H borylation of (hetero)arenes

Scheme 14. Supermolecular iridium catalysis for meta-selective C—H borylation of pyridines

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