Iridium(III)-catalyzed remote B(9)−H alkylation of o-carboranes with nitrile template DOI Creative Commons
Phil Ho Lee, Kyungsup Lee, Ji‐Won Kim

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 24, 2024

Abstract Although the directing group assisted ortho-B − H activation reactions of o-carboranes have been well established during past decade, meta-B are unexplored so far. Herein, iridium(III)-catalyzed remote B(9) alkylation with nitrile template demonstrated for first time. It was revealed that fine tuning structures is essential high reaction efficiency and regioselectivity. This process exhibits a broad substrate scope good functional tolerance under simple conditions. The template, readily accessible from o-carborane acids, can be removed conveniently after completion reaction. present method provides powerful synthetic route to complex derivatives, demonstrating successful larger scale further molecular transformations B(9)-alkylated products.

Language: Английский

Directing Group Assisted Transition Metal Catalyzed Selective BH Functionalization of o-Carboranes DOI
Zuowei Xie, Jie Zhang

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: June 11, 2024

Abstract Carboranes are a type of molecular clusters consisting carbon, hydrogen, and boron atoms. They possess unique characteristics, such as three-dimensional aromaticity, icosahedral geometry, robustness. Functionalized carboranes have been utilized in various fields, including medicine, materials, organometallic/coordination chemistry. In this context, selective functionalization o-carboranes has received tremendous attention, specifically the regio- enantioselective modification ten chemically similar BH vertices within carborane cage. recent years, significant progress made catalytic vertex-specific functionalization, well achieving cage BH. This review provides an overview advancements research field. 1 Introduction 2 Carboxy-Assisted Functionalization 2.1 Formation B–C Bonds 2.2 B–N 2.3 B–O 2.4 B–X 2.5 Consecutive B–Y (Y = N, O) 3 N-Based Directing-Group-Assisted B–H 3.1 Acylamino Directing Group 3.2 Amide 3.3 Pyridyl 3.4 Imine 4 Phosphinyl-Assisted Cage 5 Bidentate-Directing-Group-Assisted 6 Other 7 Conclusions

Language: Английский

Citations

3
Regiocontrollable B(2/3)–H Alkenylation of nido-Carboranes DOI
Ping Li, Jiayi Yang,

Jiayi Zeng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

Anionic

Citations

3
Enantioselective Alkenylation of o-Carboranes via Ir-Catalyzed Asymmetric B–H Activation DOI Creative Commons
Huifang Zhang, Jie Zhang, Zaozao Qiu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(21), P. 13856 - 13862

Published: Oct. 12, 2023

The intrinsic chirality of three-dimensional carborane derivatives is established by the substitution patterns on icosahedral cage, which much less studied than planar, axial, central, and helical observed in organic synthesis. Based transition-metal-catalyzed asymmetrical B–H activation methodology, addition functional groups can change symmetrical o-carborane to chiral-at-cage structures. Herein, we report an asymmetric boron vertex alkenylation 3-acylamino-o-carboranes with diarylacetylenes for developing cage (S)-B(4)/(R)-B(7) enantioselectivity o-carborane. A high efficiency up 99% ee be achieved Ir-catalyst-promoted (S)-B(4)–H under mild reaction conditions. enantiocontrol model suggested basis DFT results where chiral phosphine ligand plays a crucial role this catalytic enantioselective

Language: Английский

Citations

7
Palladium-Catalyzed Regioselective B(3,5)-Dialkenylation and B(4)-Alkenylation of o-Carboranes DOI Creative Commons
Shasha Yuan, Huifang Zhang, Zaozao Qiu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2474 - 2479

Published: Feb. 2, 2024

Picolyl group directed B(3,5)-dialkenylation and B(4)-monoalkenylation of

Language: Английский

Citations

2
Reactions with sulfoxonium ylides using metal-catalysis DOI
Marcio Hayashi, Viktor Saraiva Câmara,

Cristhian S. Oliveira

et al.

Advances in organometallic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 227 - 286

Published: Jan. 1, 2024

Language: Английский

Citations

0
Rhodium(III)-Catalyzed B(4)-Azo Coupling of o-Carboranes with Aryl Diazonium Tetrafluoroborates DOI
Kyungsup Lee, S.‐K. YOON, Hee Chan Noh

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

Rh(III)-catalyzed B(4)-azo coupling reactions of

Language: Английский

Citations

0
Iridium(III)-catalyzed remote B(9)−H alkylation of o-carboranes with nitrile template DOI Creative Commons
Phil Ho Lee, Kyungsup Lee, Ji‐Won Kim

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 24, 2024

Abstract Although the directing group assisted ortho-B − H activation reactions of o-carboranes have been well established during past decade, meta-B are unexplored so far. Herein, iridium(III)-catalyzed remote B(9) alkylation with nitrile template demonstrated for first time. It was revealed that fine tuning structures is essential high reaction efficiency and regioselectivity. This process exhibits a broad substrate scope good functional tolerance under simple conditions. The template, readily accessible from o-carborane acids, can be removed conveniently after completion reaction. present method provides powerful synthetic route to complex derivatives, demonstrating successful larger scale further molecular transformations B(9)-alkylated products.

Language: Английский

Citations

0