铱催化的(杂)芳烃远端区域选择性C—H硼化反应的最新进展

doi:10.6023/cjoc202103020

摘要/Abstract

(杂)芳基硼酸及其衍生物在合成化学、材料科学和药物化学领域具有广泛的用途, 因此, 其合成方法研究一直备受关注. 铱催化的C—H硼化反应是合成这类化合物最为有效的途径之一, 然而, 由于反应机理的限制, 区域选择性可控的C—H硼化是铱催化体系的一大挑战, 同时也是该领域的一个重要发展方向. 系统介绍了最近几年铱催化的芳烃远端硼氢化反应的最新进展.

关键词: 碳氢键活化, (杂)芳基硼酸酯, 合成方法, 硼化

(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

引用此文

邹晓亮, 徐森苗. 铱催化的(杂)芳烃远端区域选择性C—H硼化反应的最新进展[J]. 有机化学, 2021, 41(7): 2610-2620.

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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图/表 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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