86487-19-6Relevant articles and documents
Illuminating Stannylation
Sakamoto, Kyoka,Nagashima, Yuki,Wang, Chao,Miyamoto, Kazunori,Tanaka, Ken,Uchiyama, Masanobu
supporting information, p. 5629 - 5635 (2021/05/04)
We have developed photoboosted stannylation reactions of terminal alkynes (linear-selective hydrostannylation) and fluoroarenes (defluorostannylation), in which the stannyl anion is photoexcited to an excited triplet (T1) stannyl diradical species. This u
Development of oxathiino[6,5-b]pyridine 2,2-dioxide derivatives as selective inhibitors of tumor-related carbonic anhydrases IX and XII
Nocentini, Alessio,Supuran, Claudiu T.,?alubovskis, Raivis,Domra?eva, Ilona,Grandāne, Aiga
supporting information, (2020/05/25)
Oxathiino[6,5-b]pyridine 2,2-dioxides are identified as a new class of isoform-selective nanomolar inhibitors of tumor associated human carbonic anhydrases (hCA) IX and XII. At the same time they do not inhibit or poorly inhibit cytosolic isoforms hCA I and II. Oxathiino[6,5-b]pyridine 2,2-dioxides exhibited good antiproliferative properties on tumor cell lines MCF-7 (Human breast adenocarcinoma), A549 (human lung (alveolar) adenocarcinoma) and HeLa (epithelioid cervix carcinoma).
Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions
Wang, Xiu,Wang, Zhenhua,Liu, Li,Asanuma, Yuya,Nishihara, Yasushi
, (2019/05/24)
Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.
Method for converting substituted sodium aryl sulfonate to aryl tri-n-butyltin
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Paragraph 0083-0088, (2018/12/14)
The invention discloses a method for converting substituted sodium acryl sulfonate to aryl tri-n-butyltin. The synthetic method of the aryl tri-n-butyltin compound comprises the following steps: uniformly mixing sodium aryl sulfonate, silver carbonate, bis(tri-tert-butylphosphine)palladium, and hexabutyldistannane in a solvent, reacting for 1 to 8 hours at 80 to 140 DEG C, and after the reaction is ended, concentrating; and performing the column chromatography, and obtaining a pure aryl tri-n-butyltin product. The adopted raw material is sodium aryl sulfonate which is significant in supplementation, wide in source, cheap and easy to obtain compared with the existing method adopting aromatic halides as a raw material. The reaction in the invention has good tolerance and universality for a functional group, and the substituent group can be hydrogen, methyl, tertiary butyl, fluorine, chlorine, bromine, cyanogroup, trifluoromethyl, nitro, acetyl or carbethoxy.
Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes
Lian, Chang,Yue, Guanglu,Zhang, Haonan,Wei, Liyan,Liu, Danyang,Liu, Sichen,Fang, Huayi,Qiu, Di
supporting information, p. 4019 - 4023 (2018/10/04)
A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.
Catalytic Ester to Stannane Functional Group Interconversion via Decarbonylative Cross-Coupling of Methyl Esters
Yue, Huifeng,Zhu, Chen,Rueping, Magnus
supporting information, p. 385 - 388 (2018/01/27)
An unprecedented conversion of methyl esters to stannanes was realized, providing access to a series of arylstannanes via nickel catalysis. Various common esters including ethyl, cyclohexyl, benzyl, and phenyl esters can undergo the newly developed decarbonylative stannylation reaction. The reaction shows broad substrate scope, can differentiate between different types of esters, and if applied in consecutive fashion, allows the transformation of methyl esters into aryl fluorides or biaryls via fluororination or arylation.
Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
Akram, Manjur O.,Shinde, Popat S.,Chintawar, Chetan C.,Patil, Nitin T.
supporting information, p. 2865 - 2869 (2018/05/03)
Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.
Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction
Horino, Yoshikazu,Sugata, Miki,Mutsuura, Itaru,Tomohara, Keisuke,Abe, Hitoshi
supporting information, p. 5968 - 5971 (2017/11/10)
Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.
METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND
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Paragraph 0085-0086; 0088, (2016/10/31)
PROBLEM TO BE SOLVED: To provide a method for quantitatively producing a group 14 metal lithium compound under a mild condition. SOLUTION: The method for producing a group 14 metal lithium compound represented by formula (4): R4-nMLin comprises reacting a compound represented by formula (1): R4-nMXn and lithium in the presence of a polycyclic aromatic compound represented by formula (2) or formula (3). [In formula (1) and formula (2), R is a hydrocarbon group; M is a metal atom selected from Si, Ge and Sn; X is a halogen atom or R3M- (R and M are the same as mentioned above); and n is 1 or 2] and [R1 is H or a hydrocarbon group; and m is an integer of 0 to 5.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
A Sn atom-economical approach toward arylstannanes: Ni-catalysed stannylation of aryl halides using Bu3SnOMe
Komeyama, Kimihiro,Asakura, Ryota,Takaki, Ken
supporting information, p. 8713 - 8716 (2015/08/24)
Stannylation of carbon-halogen bonds is one of the most promising and straightforward approaches for the preparation of organostannane compounds. Although a wide variety of methods are now available, all protocols require the use of highly nucleophilic organometals or wasteful stannyl sources like distannanes. Here, we report a new nickel-catalysed stannylation of aryl and alkenyl-halides using Bu3SnOMe as a stannyl source to afford aryl and vinyl-stannanes, respectively. This method enables the stannylation of not only bromides, but also chlorides and triflates to furnish functionalized aryl- and alkenyl-stannanes without the release of wasteful and toxic stannyl byproducts.
