Synthesis of 1-Substituted Bicyclo[2.1.1]hexan-2-ones via a Sequential SmI2-Mediated Pinacol Coupling and Acid-Catalyzed Pinacol Rearrangement Reaction
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DOI: 10.1021/acs.orglett.4c03541
Abstract: A two-step procedure, combining a SmI2-mediated transannular pinacol coupling reaction with an acid-catalyzed pinacol rearrangement process, was employed to prepare a diverse range of 1-substituted bicyclo[2.1.1]hexan-5-ones from cyclobutanedione derivatives. To underscore the significance of these… read more here.
Keywords: substituted bicyclo; acid catalyzed; catalyzed pinacol; pinacol rearrangement ... See more keywords
Assignment of the Crystal Structure to the Aza-Pinacol Coupling Product by X-ray Diffraction and Density Functional Theory Modeling
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DOI: 10.1021/acsomega.2c05446
Abstract: Aza-pinacol coupling of N-benzyl-1-phenylmethanimine using Zn dust affords a mixture of R,S- or R,R-diastereomers in a 1:1 ratio. The R,S-diastereomer is solid with an m.p. of 135 °C, while the R,R-diastereomer is liquid at room… read more here.
Keywords: functional theory; pinacol coupling; ray; diffraction density ... See more keywords
Plasma Electrochemistry for Carbon-Carbon Bond Formation via Pinacol Coupling.
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DOI: 10.1021/jacs.3c01779
Abstract: The formation of carbon-carbon bonds by pinacol coupling of aldehydes and ketones requires a large negative reduction potential, often realized with a stoichiometric reducing reagent. Here, we use solvated electrons generated via a plasma-liquid process.… read more here.
Keywords: plasma electrochemistry; pinacol coupling; carbon; electrochemistry ... See more keywords
Diastereoselective and enantioselective photoredox pinacol coupling promoted by titanium complexes with a red-absorbing organic dye
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DOI: 10.1039/d2sc00800a
Abstract: The pinacol coupling reaction, a reductive coupling of carbonyl compounds that proceeds through the formation of ketyl radicals in the presence of an electron donor, affords the corresponding 1,2-diols in one single step. The photoredox… read more here.
Keywords: red absorbing; pinacol coupling; pinacol; absorbing organic ... See more keywords