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sigmatropic rearrangements of B(MIDA)-propargylic alcohols towards the diverse synthesis of α-functionalized organoborons

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Science China Chemistry 2024年第2期67卷 568-575页

作者： Jiasheng Qian Li-Cai Liu Zhi-Hao Chen Yuan Liu Yin Li Qingjiang Li Honggen Wang Guangdong Key Laboratory of Chiral Molecule and Drug Discovery School of Pharmaceutical SciencesSun Yat-Sen UniversityGuangzhou510006China

α-Functionalized organoborons are useful building blocks and key structural elements in functional molecules.Their previous synthesis relied on the famous Matteson reaction or the late-stage borylative modification of alkynes or alkenes.Recently,the synthetic transformation of borylated building blocks offers another useful strategy and is currently actively explored.We report herein that B(MIDA)-propargylic alcohols(BPAs) are a useful type of borylated building blocks.Bearing two complementary functional group handles(alkyne and hydroxyl) in close proximity,the redox-neutral [3,3] and [2,3] sigmatropic rearrangements of BPAs allow the efficient synthesis of several types of α-functionalized boronates,including α,β-unsaturated acylborons,α-S/P-substituted allenylborons,boryl-substituted thiazoles and a borylated α,β-unsaturated hydrazine,some of which are otherwise challenging targets using other synthetic methods.

关键词： organoboron diverse synthesis sigmatropic rearrangement heteroarene amide

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Catalyst-Free Imidation of Allyl Sulfides with Chloramine-T and Subsequent [2,3]-sigmatropic rearrangement

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Chinese Journal of Chemistry 2012年第9期30卷 2029-2035页

作者：江玉波莫凡洋邱迪匡春香张艳王剑波 Department of Chemistry Tongji UniversityShanghai 200092China Faculty of Science Kunming University of Science and TechnologyKunmingYunnan 650093China Beijing National Laboratory of Molecular Sciences(BNLMS)and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of ChemistryPeking UniversityBeijing 100871China

A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine-T and sub- sequent [2,3]-sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under this condition.

关键词： allyl sulfonamide allyl sulfide transition-metal-free reaction sigmatropic rearrangement nitrene

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Congestion-Accelerated [3,3]-sigmatropic rearrangement towards Synthesis of α-Aryl Nitriles

Congestion-Accelerated [3,3]-Sigmatropic Rearrangement towar...

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中国化学会·第十五届全国有机合成化学学术研讨会

作者：赵伟钊彭勃浙江师范大学

α-Aryl nitriles are recurrent motifs in drugs and other bioactive compounds. They can also be readily converted to α-aryl carboxylic acids, amides, aldehydes, amines, ketones, and heterocycles. In 2017, we serendipitously discovered a new approach to α-aryl nitriles by sequentially treating a mixture of arylsulfoxides and alkylnitriles with TfO and organic base(eq 1, Fig.1). Mechanistic studies indicate that a [3,3]-sigmatropic rearrangement of arylsulfonium ketenimine as a key step is involved in the reaction.Inspired by this discovery, we recently developed a robust ortho C-H cyanoalkylation of aryliodanes(eq 2, Fig.1). This reaction can proceed under-78 ℃ and complete in 5 min.Such low temperature and short reaction time give the process excellent functional group compatibility and broad substrate scope.We believe the advent of both redox-neutral reactions will inspire the development of [3,3]-sigmatropic rearrangement by making use of the congestion release of ketenimine moieties of rearrangement precursors.

关键词： sigmatropic rearrangement cyanoalkylation arylsulfoxide hypervalent iodine

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Applicableβ-Sulfonium Carbanions: Facile Metal-Free Construction of Thiophene Derivatives

Applicableβ-Sulfonium Carbanions: Facile Metal-Free Constru...

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中国化学会全国第十二届有机合成化学学术研讨会

作者：邢刚冬姚金忠周宏伟生物与化学工程学院嘉兴学院浙江大学化学系

β-Sulfonium carbanions,as a member of organosulfur family,are ephemeral intermediates and difficult to be applied in organic synthesis.We developed a new strategy to relatively stable β-sulfonium carbanions,achieved by an intramolecular addition of a sulfur atom of sulfide to the in situ generated electron-deficlent allene moiety.These kinds of applicable β-sulfonium carbanions may imply an unexplored area,in which a bundle of synthetically useful building blocks are underground.

关键词： β-Sulfonium carbanions thiophene derivatives propargyl-allenyl isomerization sigmatropic rearrangement sigmatropic rearrangement

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