Low-Temperature Borylation of C(sp³)–O Bonds of Alkyl Ethers by Gold–Metal Oxide Cooperative Catalysis

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Since ether moieties are often found not only in petrochemical products but also natural organic molecules, the development of methods for manipulating C-O bonds ethers is important expanding range compound libraries synthesized from biomass resources, which should contribute to goal carbon neutrality. We report herein that gold nanoparticles supported on Lewis acidic metal oxides, namely α-Fe

Language: Английский

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Formal Transesterification Reaction of But-3-enyl Esters Enabled by a Synergistic Nickel/Zinc Relay

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 27, 2025

The transition metal-catalyzed coupling reaction has renewed the role of ester as an electrophilic partner. In this context, we describe a synergistic Ni/Zn-catalyzed formal transesterification but-3-enyl esters with tetrahydrofuran and alkyl iodides to give 4-alkoxylbutyl esters. aromatic aliphatic are both competent electrophiles thus broaden substrate scope in reactions, because previously reported work were strictly limited ones. Mechanistic studies reveal that C(acyl)-O bond or even more inert C(alkyl)-O could be cleaved under nickel catalysis. Two catalytic cycles proposed, which represent new pathway versus traditional transesterification.

Language: Английский

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Hydrosilylation or Dehydrogenative Silylation Pathways via the Au-Catalyzed Activation of Hydrosilanes

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123546 - 123546

Published: Jan. 1, 2025

Language: Английский

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Nanoporous gold-catalyzed borylation of C(sp3)–O bonds in dialkyl ethers and its mechanistic elucidation

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Selective cleavage and functionalization of C–O bonds in ethers is a longstanding challenge organic synthesis due to their inherent stability. This particularly significant for synthesizing alkylboron compounds, which serve as versatile intermediates diverse transformations. However, the high chemical stability dialkyl makes successful borylation rare. Herein, we present heterogeneous catalytic various with B₂pin₂ using an unsupported nanoporous gold catalyst (AuNPore). The nanosized, sponge-like operates without need metal oxide supports or bases, efficiently converting wide range acyclic cyclic ethers, well acetals, into alkyl monoboronates diboronates. Mechanistic studies indicate that AuNPore promotes B–B bond cleavage, leading deoxygenative carbocation formation. enables unprecedented pathway via formation C(sp³)–Au–Bpin organogold species, undergoes reductive elimination yield products.

Language: Английский

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Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110503 - 110503

Published: Sept. 1, 2024

Language: Английский

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