Radical hydroboration for the synthesis of organoboron compounds

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(32), P. 4275 - 4289

Published: Jan. 1, 2024

This review describes the recent research on radical hydroboration, which covers different boron sources including N-heterocyclic carbene borane, bis(pinacolato)diboron and pinacolborane, as well strategies in boryl generation.

Language: Английский

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Diastereoselective dearomatization of indoles via photocatalytic hydroboration on hydramine-functionalized carbon nitride

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 22, 2024

Abstract A protocol for trans -hydroboration of indole derivatives using heterogeneous photocatalysis with NHC-borane has been developed, addressing a persistent challenge in organic synthesis. The protocol, leveraging high crystalline vacancy-engineered polymeric carbon nitride as catalyst, enables diastereoselective synthesis, expanding substrate scope and complementing existing methods. approach emphasizes eco-friendliness, cost-effectiveness, scalability, making it suitable industrial applications, particularly renewable energy contexts. catalyst’s superior performance, attributed to its rich carbon-vacancies well-ordered structure, surpasses more expensive homogeneous alternatives, enhancing viability large-scale use. This innovation holds promise synthesizing bioactive compounds materials relevant medicinal chemistry beyond.

Language: Английский

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NHC-BH₃-Mediated Reduction of Sulfonyl Hydrazides into Disulfides and Further Cross-Coupling with Chlorostibine and Bioactivities

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

This paper presents a novel NHC-BH3-promoted one-step synthesis of disulfides and stibine sulfides using odorless sulfonyl hydrazides. The protocol tolerates various functional groups as well heterocyclic compounds. Mechanistic studies show that NHC-BH3 plays two roles: (1) reducing hydrazides into (2) promoting the cross-coupling chlorostibine with disulfides. synthesized also exhibit satisfactory anticancer activity against 4T1 MDA-MB-231 cancerous cells.

Language: Английский

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Access to tetrahydrocarbazoles via a photocatalyzed cascade decarboxylation/addition/cyclization reaction

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6694 - 6699

Published: Jan. 1, 2024

An efficient photocatalyzed decarboxylative coupling of indolepropionic acid NHPI esters with α,β-unsaturated carbonyl compounds has been developed, which provided structurally diverse tetrahydrocarbozles in moderate to good yields.

Language: Английский

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Recent Advances in Photoinduced Borylation via N-Heterocyclic Carbene Boryl Radicals

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

Published: Aug. 28, 2024

Abstract Organoboron compounds are recognized as essential synthetic intermediates in organic chemistry and have found broad applications pharmaceutical materials science. In recent years, the development of novel boronating reagents has opened new avenues for synthesis organoboron compounds. Among these, N-heterocyclic carbene boranes (NHC-boranes), with their unique advantages, garnered sustained interest evolved into important precursors boron-centered radicals, participating a diverse array visible-light-induced borylation reactions. This short review primarily focuses on radical reactions involving NHC-boranes, summarizing latest advancements field offering inspiration subsequent research. 1 Introduction 2 Photoinduced Borylation via NHC-Boryl Radicals 2.1 Polyfluoroarenes 2.2 Arenes 2.3 Alkenes 2.4 Alkynes 2.5 Other Substrates 3 Conclusion Future Prospects

Language: Английский

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Complexes of Borane and 1,3,5‐Triazinane‐Derived Carbenes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2483 - 2488

Published: April 11, 2024

Abstract Complexes of borane with six‐membered N‐heterocyclic carbenes derived from readily accessible 1,3,5‐triazinium salts are described. Similar to the widely used imidazolium‐type complex, obtained complexes behave as agents for hydrogen atom transfer in Giese reaction and sources boryl radicals addition imines. The amine nitrogen these does not undergo alkylation, but it can bind another molecule.

Language: Английский

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Hydrometallation of C C and C C Bonds. Group-3

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

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Functionalization of Boranes through Thiol/Oxygen Catalysis^†

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(22), P. 2804 - 2810

Published: July 17, 2024

Comprehensive Summary A greener and more convenient alternative to traditional methods for the generation of thiyl radical as hydrogen atom transfer (HAT) catalyst is developed, using molecular oxygen oxidize thiol without need chemical initiators or light irradiation. The thiol/oxygen catalysis enables selective efficient difunctionalization borane.

Language: Английский

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Visible-Light-Mediated Radical trans-Hydroboration of Alkynes with NHC Borane

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

Although the radical hydroboration of alkenes with N-heterocyclic carbene (NHC) borane is well documented, alkynes, especially terminal remains challenging. Herein, a photoredox-catalyzed trans-hydroboration alkynes NHC has been developed, which provided various alkenyl boron compounds in moderate to good yields. This protocol exhibits broad substrate scope, as both internal and were compatible. The synthetic value this method was further demonstrated by its applicability late-stage modification bioactive molecules. A preliminary mechanism for reaction proposed.

Language: Английский

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