1326317-68-3Relevant academic research and scientific papers
Direct Conversion of Carboxylic Acids to Alkyl Ketones
Amani, Javad,Molander, Gary A.
, p. 3612 - 3615 (2017)
An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated c
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.
Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides
Amani, Javad,Alam, Rauful,Badir, Shorouk,Molander, Gary A.
supporting information, p. 2426 - 2429 (2017/05/12)
An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N-C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups.
Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis
Amani, Javad,Molander, Gary A.
, p. 1856 - 1863 (2017/02/10)
Visible light photoredox/nickel dual catalysis has been employed in the cross-coupling of acyl chlorides with potassium alkyltrifluoroborates. This protocol, based on single-electron-mediated alkyl transfer, circumvents the restriction of using reactive alkylmetallic nucleophiles in transition-metal-catalyzed acylation and achieves a mild and efficient method for the synthesis of unsymmetrical alkyl ketones. In this approach, a variety of acyl chlorides have been successfully coupled with structurally diverse potassium alkyltrifluoroborates, generating the corresponding ketones with good yields.
Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane
Molander, Gary A.,McKee, Silas A.
supporting information; experimental part, p. 4684 - 4687 (2011/11/06)
The copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-unsaturated amides are converted to the corresponding β-trifluoroboratoamides in good to excellent yields. The β-boration of a variety of α,β-unsaturated esters and ketones is also reported.
