165904-32-5Relevant articles and documents
Hexamethyldisilazane Lithium (LiHMDS)-Promoted Hydroboration of Alkynes and Alkenes with Pinacolborane
Liu, Jichao,Wu, Caiyan,Hu, Tinghui,Yang, Wei,Xie, Yaoyao,Shi, Yinyin,Liu, Qianrui,Shao, Yinlin,Zhang, Fangjun
, p. 3442 - 3452 (2022/02/23)
Lithium-promoted hydroboration of alkynes and alkenes using commercially available hexamethyldisilazane lithium as a precatalyst and HBpin as a hydride source has been developed. This method will be appealing for organic synthesis because of its remarkable substrate tolerance and good yields. Mechanistic studies revealed that the hydroboration proceeds through the in situ-formed BH3species, which acts to drive the turnover of the hydroboration of alkynes and alkenes.
Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies
Ton, Nhan N. H.,Mai, Binh Khanh,Nguyen, Thanh Vinh
, p. 9117 - 9133 (2021/07/19)
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.
Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration
Garhwal, Subhash,Kroeger, Asja A.,Thenarukandiyil, Ranjeesh,Fridman, Natalia,Karton, Amir,De Ruiter, Graham
supporting information, p. 494 - 504 (2021/01/11)
In the past decade, the use of earth-abundant metals in homogeneous catalysis has flourished. In particular, metals such as cobalt and iron have been used extensively in reductive transformations including hydrogenation, hydroboration, and hydrosilylation
