Cobalt-Catalyzed Aerobic Cross-Dehydrogenative Coupling of C–H and Thiols in Water for C–S Formation

Huang, Xin; Chen, Yongqi; Zhang, Shan; Song, Lijuan; Gao, Mingqi; Zhang, Panke; Li, Heng; Yuan, Bingxin; Yang, Ge

doi:10.1021/acs.joc.7b02718

Cited by 83 publications

(57 citation statements)

References 73 publications

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“…The hydroxyl group of A was converted to an ortho-metallation directing MOMO group [7] by reaction with dimethoxymethane in the presence of P 2 O 5 [9] to give B. Treatment of B with nBuLi followed by addition of DMF and then aqueous work up produced compound C. [7,10] Removal of the MOM group of C in the presence of concentrated HCl gave the desired product 5.…”

Section: Resultsmentioning

confidence: 99%

O‐Alkylation of 3‐Formyl‐BINOL and Its Strong Effect on the Fluorescence Recognition of 1,3‐Diaminopropane

Wang

Sheng

et al. 2018

Eur J Org Chem

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Systematic alkylation of the hydroxyl groups of 3‐formyl‐1,1′‐bi‐2‐naphthol (3‐formyl‐BINOL) has been conducted to generate four BINOL‐based aldehydes 2–5. These compounds differ in the number and position of ethyl group at the two BINOL hydroxyl groups. Their fluorescence response toward various amines and diamines has been studied. It is found that when the hydroxyl group ortho to the aldehyde is alkylated, the resulting compounds 3 and 4 become highly selective molecular probes for 1,3‐diaminopropane (DAP), a biologically significant diamine, with large fluorescence enhancement. However, compound 2 that has no O‐alkyl group and compound 5 that is only alkylated at the hydroxyl group distal to the aldehyde do not show large fluorescence enhancement. Through NMR and mass spectroscopic analyses, it is revealed that the imine products formed from the reactions of 2 and 5 with DAP can be stabilized by an intramolecular bonding interaction and give only weak fluorescence. Compounds 3 and 4 whose ortho‐hydroxyl groups are alkylated react with DAP to form cyclic aminals to give greatly enhanced fluorescence.

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Section: Resultsmentioning

confidence: 99%

O‐Alkylation of 3‐Formyl‐BINOL and Its Strong Effect on the Fluorescence Recognition of 1,3‐Diaminopropane

Wang

Sheng

et al. 2018

Eur J Org Chem

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“…The BINOL-based aldehyde 1 is readily prepared from the methoxymethyl-protected (S)-BINOL by ortho-metalation with nBuLi followed by the addition of N,N-dimethylformamide (DMF) and then acidic hydrolysis (Scheme 1). [11] It shows very weak fluorescence and minimal fluorescence response toward various primary amines and diamines in the absence of Zn II ions. [12] This compound cannot be used directly for the fluorescent recognition of these substrates.…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Recognition of 1,3‐Diaminopropane in the Fluorous Phase – Greatly Enhanced Sensitivity and Selectivity

et al. 2018

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A 1,1′‐binaphthyl‐based dialdehyde, which is soluble in the fluorous phase, is synthesized. The fluorescence of this compound is greatly enhanced by 1,3‐diaminopropane (DAP) in perfluorohexane (FC‐72) but not by other amines and diamines. Thus, this compound can be used as a fluorescent sensor for the detection of the biologically important DAP at submicromolar concentrations. The selectivity and sensitivity of this fluorescent probe in this fluorous solvent are much greater than those in the common organic solvent dichloromethane.

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“…Interestingly,the group of Xu describedin2018the first aerobic copper-catalyzedo xidative trifunctionalization of styrenes (265) via benzenethiosulfonates (7)f or the synthesiso fa-sulfenyl b-keto sulfones (274). [195] The copper catalyst facilitates the production of ab enzenesulfonyl radical (229), which than reacts with an olefin. Subsequent trappingw ith molecular oxygen and fragmentation of the generatedp eroxy Cu(II) complex 276 produces a b-keto sulfone (277), which is a-sulfenylated in the final step via reductive elimination.…”

Section: Radical Sulfenylations and Sulfonylationmentioning

confidence: 99%

Thiosulfonates as Emerging Reactants: Synthesis and Applications

et al. 2019

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The synthetic strategies towards thiosulfonates (RSO2SR1) are comprehensively reviewed from their original discovery to recent advances. Incorporation of the green credentials of the synthetic procedures towards thiosulfonates allows one to judge the merits of the state of the art, beyond the typical yield of a product and availability of the reactants. As reactant for organic transformations, thiosulfonates are particularly interesting given their possibility to react with nucleophiles, electrophiles and radicals. This review aims to give researchers, not familiar with the field, a good understanding of the general applications of thiosulfonates, while not skipping the recent important advances. The related, but less explored, selenosulfonates (RSO2SeR1) are also covered.

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Cobalt-Catalyzed Aerobic Cross-Dehydrogenative Coupling of C–H and Thiols in Water for C–S Formation

Cited by 83 publications

References 73 publications

O‐Alkylation of 3‐Formyl‐BINOL and Its Strong Effect on the Fluorescence Recognition of 1,3‐Diaminopropane

O‐Alkylation of 3‐Formyl‐BINOL and Its Strong Effect on the Fluorescence Recognition of 1,3‐Diaminopropane

Fluorescent Recognition of 1,3‐Diaminopropane in the Fluorous Phase – Greatly Enhanced Sensitivity and Selectivity

Thiosulfonates as Emerging Reactants: Synthesis and Applications

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