63076-51-7Relevant articles and documents
Practical and Modular Construction of C(sp3)-Rich Alkyl Boron Compounds
Yang, Yangyang,Tsien, Jet,Ben David, Ayala,Hughes, Jonathan M. E.,Merchant, Rohan R.,Qin, Tian
, p. 471 - 480 (2021/01/13)
Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method is extensively examined through a variety of substrates, including synthesis and late-stage functionalization of scaffolds relevant to medicinal chemistry. The strategic significance of this approach, with alkyl boronic acids as linchpins, is demonstrated through various downstream functionalizations of the alkyl boron compounds. This two-step concurrent cross-coupling approach, resembling formal and flexible alkyl-alkyl couplings, provides a general entry to synthetically challenging high Fsp3-containing drug-like scaffolds.
Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis
Liu, Mingshang,Huang, Hanchu,Chen, Yiyun
supporting information, p. 1209 - 1212 (2018/11/06)
All-carbon quaternary centers are prevalent in bioactive small molecules. However, their efficient construction remains a formidable synthetic challenge. Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing α-quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent-allylic alcohol complex, which enables the first alkyl boronate addition and semi-pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation. The reaction is suitable for gram scale synthesis and is transformable to alcohols, olefins, oximes, and lactones with an α-quaternary center in one step.
Dichloroborane-dioxane: An exceptional reagent for the preparation of alkenyl- and alkylboronic acids
Josyula, Kanth V. B.,Gao, Peng,Hewitt, Chris
, p. 7789 - 7792 (2007/10/03)
Terminal alkynes and alkenes were conveniently hydroborated to the corresponding alkenyl- and alkyldichloroboranes using dichloroborane-dioxane in dichloromethane. These dichloroboranes were hydrolyzed by water to the corresponding alkenyl- and alkylboron