1070704-04-9Relevant articles and documents
Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies
Mai, Binh Khanh,Nguyen, Thanh Vinh,Ton, Nhan N. H.
, p. 9117 - 9133 (2021)
Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.
Selective electrocatalytic hydroboration of aryl alkenes
Zhang, Yahui,Zhao, Xiangyu,Bi, Ce,Lu, Wenqi,Song, Mengyuan,Wang, Dongdong,Qing, Guangyan
supporting information, p. 1691 - 1699 (2021/03/09)
Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chemistry, and transition metal-catalysed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more eco
Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide
Weng, Wei-Zhi,Liang, Hao,Zhang, Bo
supporting information, p. 4979 - 4983 (2018/08/24)
A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.
