Regioselective Transition-Metal-Free Arene C-H Borylations: From Directing Groups to Borylation Template Reagents

Review Chemistry, Multidisciplinary

Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C-H Bonds

Bo Su et al.

Summary: This review discusses the rapid development and significance of enantioselective silylation and borylation of C-H bonds, emphasizing the importance of designing and developing chiral ligands for these reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Metal-Free Phosphorus-Directed Borylation of C(sp2)-H Bonds

Omar Sadek et al.

Summary: A new method has been developed for the synthesis of phosphine-boranes, featuring simplicity, efficiency, and broad substrate scope. The key intermediates were identified as P-stabilized borenium cations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

BBr3-Mediated P(III)-Directed C-H Borylation of Phosphines

Jiahang Lv et al.

Summary: The study developed a metal-free P(III)-directed phosphine C-H borylation method, mediated by BBr3, to synthesize products containing both phosphorus and boron. The metal-free strategy features low cost, practicality, and environmental friendliness.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Article Chemistry, Multidisciplinary

A free boratriptycene-type Lewis superacid

Marcel Henkelmann et al.

Summary: Bicyclic pyrazabole-bridged ferrocenes with BH groups at their bridgehead positions were successfully synthesized, showing a very short Fe...B(sp(2)) distance. Experimental and theoretical assessments confirmed that the compound is among the strongest boron-based Lewis acids available to date.

CHEMICAL SCIENCE (2022)

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Review Chemistry, Multidisciplinary

Transition-Metal-Free Heterocyclic Carbon-Boron Bond Formation

Subrata Hazra et al.

Summary: This article summarizes the current research status and methods of transition-metal-free synthesis of heteroaryl boronic acids and esters. The transition-metal-free synthesis methods are environmentally friendly, economically advantageous, and have replaced transition-metal-based synthesis methods.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Article Chemistry, Multidisciplinary

Borylation Directed Borylation of Indoles Using Pyrazabole Electrophiles: A One-Pot Route to C7-Borylated-Indolines

Jurgen Pahl et al.

Summary: In this research, a new diboron compound, Pyrazabole (1), was discovered, which can be transformed into ditopic electrophiles. The unique B center dot center dot center dot B separation in 1 enables double E-H functionalization of indoles and indolines. Specifically, the activation of 1 with HNTf2 generates an electrophile that can convert N-H indoles and indolines into N/C7-diborylated indolines.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Regioselective Transition-Metal-Free C(sp2)-H Borylation: A Subject of Practical and Ongoing Interest in Synthetic Organic Chemistry

Supriya Rej et al.

Summary: Considerable advances have been made in the field of C-H functionalization, with special interest in C-H borylation due to its wide applications. Transition-metal-catalyzed regioselective strategies have been developed, but the use of precious metals and contamination by metal precursors limit their application in large-scale synthesis. Recent trends involve the use of transition-metal-free systems.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Metal-catalysed C-H bond activation and borylation

Ranjana Bisht et al.

Summary: Transition metal-catalysed direct borylation of hydrocarbons via C-H bond activation has gained significant attention for its synthetic versatility. Selectivity control is a challenging issue, but recent efforts have led to impressive progress in both proximal and distal C-H bond borylation reactions. Innovative methodologies have been developed for ortho C-H bond borylation reactions, while meta and para selective reactions remain a challenge. Advancements have also been made for aliphatic C(sp(3))-H borylations and enantioselective borylations. This review discusses the development of different approaches and findings since 2014, as well as various applications of C-H borylation reactions in the synthesis of natural products, therapeutics, and materials chemistry.

CHEMICAL SOCIETY REVIEWS (2022)

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Review Chemistry, Multidisciplinary

Iridium-Catalysed C-H Borylation of Heteroarenes: Balancing Steric and Electronic Regiocontrol

Jay S. Wright et al.

Summary: The review focuses on the borylation of heteroarenes, with an emphasis on the influence of steric and electronic effects on regiochemical outcome. It is shown that the borylation of heterocyclic substrates is more challenging, with the position and nature of the heteroatoms significantly affecting the reactivity and regioselectivity of the reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Metal-Free Directed C-H Borylation of Pyrroles

Zheng-Jun Wang et al.

Summary: The research presents a general strategy for site-selective C-H borylation of pyrroles using BBr3 directed by pivaloyl groups, without the need for any metal catalysts. The reaction is influenced by chelation and electronic effects, leading to diverse products with high positional selectivity and downstream transformation capabilities. DFT calculations confirm the preferred positional selectivity of this reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Photoinduced Borylation for the Synthesis of Organoboron Compounds Focus Review

Ya-Ming Tian et al.

Summary: This review summarizes the research on photoinduced borylations, focusing on recent developments and trends. Studies cover the catalytic methods, substrates, and reaction mechanisms of boronations.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Transient Imine as a Directing Group for the Metal-Free o-C-H Borylation of Benzaldehydes

Supriya Rej et al.

Summary: Organoboron reagents play a crucial role in synthetic organic chemistry, and current selective borylation strategies rely heavily on transition-metal catalysts. However, this study introduces a transition-metal-free approach for selective C-H borylation of electron-deficient benzaldehyde derivatives, demonstrating effectiveness even in the presence of external impurities.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Pyrimidine-directed metal-free C-H borylation of 2-pyrimidylanilines: a useful process for tetra-coordinated triarylborane synthesis

Supriya Rej et al.

Summary: This study presents a metal-free directed ortho-C-H borylation of 2-pyrimidylaniline derivatives, leading to the synthesis of various boronates and triarylborane derivatives. The reaction proceeds smoothly without interference by external impurities, highlighting its importance in synthetic chemistry.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary