Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

Yang, Guang; Xiong, Zhicheng; Nie, Hongsheng; He, Meiqin; Feng, Qiong; Li, Xuan; Huang, Huabin; Wang, Shoucai; Ji, Fanghua; Jiang, Guang-Bin

doi:10.1021/acs.orglett.2c00454

Cited by 11 publications

(4 citation statements)

References 45 publications

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“…In the past decade, transition-metal-catalyzed inert C–H activations have been proven to be powerful strategies for many useful transformations and organic synthesis . Meanwhile, the directing-group-assisted C–H activation strategy has attracted significant attention .…”

Section: Introductionmentioning

confidence: 99%

Electrochemically Driven Selective Removal of the S═N Bond-Directing Group Using Cyclohexanone Oxime as the Mediator

et al. 2023

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An inexpensive electrochemical induction system was used for the efficient reductive defunctionalization of sulfoximines through a radical pathway. This practical and robust strategy could be used for the removal of the SN bond-directing group from various sulfoximines. The practicability of this method was demonstrated by its mild conditions, simple operation, one-pot procedure, gram-scale synthesis, and the undivided cell. Furthermore, preliminary mechanistic studies suggested that the reaction might proceed via a homocoupling reaction and a denitrification procedure.

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Section: Introductionmentioning

confidence: 99%

Electrochemically Driven Selective Removal of the S═N Bond-Directing Group Using Cyclohexanone Oxime as the Mediator

et al. 2023

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“…The latest advances with the insertion of SO 2 concentrate on the radical process, and a series of radical precursors including phenylpropynoates, electron-deficient olefins, and indolyl-ynones were used for SO 2 insertion, inducing the formation of sulfonyl radical intermediates. Inspired by this outstanding work and as part of our ongoing interest in organic synthetic chemistry, herein, we reported a copper-catalyzed N–H sulfonylation reaction of sulfoximines, aryldiazonium tetrafluoroborates, and DABSO, providing the N -sulfonyl sulfoximines in high yields under mild conditions (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Sulfonylation Reaction of NH-Sulfoximines with Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: Formation of N-Sulfonyl Sulfoximines

Nie

Xiong

et al. 2023

J. Org. Chem.

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An efficient and practical SO 2 insertion protocol of NH-sulfoximines with aryldiazonium tetrafluoroborates and DABSO toward N-sulfonyl sulfoximines has been developed under mildly basic conditions. This transformation features easy operation, readily available substrates, and mild conditions. A tentative mechanism is proposed, which indicates that the aryldiazonium tetrafluoroborates would be radical donors under standard reaction conditions. The aryl radical produced in situ from diazonium salts would be trapped by SO 2 to generate an arylsulfonyl radical and then undergo further transformation to generate the final N-sulfonyl sulfoximines.

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“…Furthermore, a genome-wide association study (GWAS) conducted using a panel of 529 rice accessions indicated that GHD7 and NAL were the major loci controlling the natural variation of chlorophyll content in rice leaves (Wang et al, 2015). Recently, GWAS was carried out for 29 rice leaf traits related to leaf size, shape, and color and unraveled several QTLs (Yang et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Multi-model genome-wide association studies of leaf anatomical traits and vein architecture in rice

et al. 2023

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IntroductionThe anatomy of rice leaves is closely related to photosynthesis and grain yield. Therefore, exploring insight into the quantitative trait loci (QTLs) and alleles related to rice flag leaf anatomical and vein traits is vital for rice improvement.MethodsHere, we aimed to explore the genetic architecture of eight flag leaf traits using one single-locus model; mixed-linear model (MLM), and two multi-locus models; fixed and random model circulating probability unification (FarmCPU) and Bayesian information and linkage disequilibrium iteratively nested keyway (BLINK). We performed multi-model GWAS using 329 rice accessions of RDP1 with 700K single-nucleotide polymorphisms (SNPs) markers.ResultsThe phenotypic correlation results indicated that rice flag leaf thickness was strongly correlated with leaf mesophyll cells layer (ML) and thickness of both major and minor veins. All three models were able to identify several significant loci associated with the traits. MLM identified three non-synonymous SNPs near NARROW LEAF 1 (NAL1) in association with ML and the distance between minor veins (IVD) traits.DiscussionSeveral numbers of significant SNPs associated with known gene function in leaf development and yield traits were detected by multi-model GWAS performed in this study. Our findings indicate that flag leaf traits could be improved via molecular breeding and can be one of the targets in high-yield rice development.

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Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

Cited by 11 publications

References 45 publications

Electrochemically Driven Selective Removal of the S═N Bond-Directing Group Using Cyclohexanone Oxime as the Mediator

Electrochemically Driven Selective Removal of the S═N Bond-Directing Group Using Cyclohexanone Oxime as the Mediator

Copper-Catalyzed Sulfonylation Reaction of NH-Sulfoximines with Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: Formation of N-Sulfonyl Sulfoximines

Multi-model genome-wide association studies of leaf anatomical traits and vein architecture in rice

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