91734-76-8Relevant academic research and scientific papers
Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle
Takale, Balaram S.,Thakore, Ruchita R.,Casotti, Gianluca,Li, Xaiohan,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 4158 - 4163 (2021/02/01)
An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.
Palladium-Catalyzed gem-Difluoroallylation Reaction between Aryltributyltin and Bromodifluoromethylated Alkenes
Chen, Chuan-Xin,Chen, Xiao-Qu,Lu, Heng,Shi, Chang-Yun,Wang, Dong-Yu,Zeng, Ruoqing,Zhang, Ao
supporting information, (2022/02/10)
A robust Stille gem-difluoroallylation of arylstannanes with 3-bromo-3,3-difluoropropenes has been established. The catalyst was found to exert critical effect on the reaction chemoselectivity. By using Pd(OH)2/C as the catalyst, a series of 3-(hetero)ary
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
Method for converting substituted sodium aryl sulfonate to aryl tri-n-butyltin
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Paragraph 0097-0102, (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.
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.
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.
Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage
Gu, Yiting,Martín, Rúben
supporting information, p. 3187 - 3190 (2017/03/17)
A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.
METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND
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Paragraph 0085; 0087-0088, (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
Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications
Wang, Dong-Yu,Wang, Chao,Uchiyama, Masanobu
supporting information, p. 10488 - 10491 (2015/09/28)
We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.
Radiohalogenation of oligonucleotides via trialkylstannylaryl conjugates
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, (2008/06/13)
Halogenated oligonucleotides and particularly radiohalogenated oligonucleotides are prepared by reacting a modified oligonucleotide with a trialkylstannylaryl reagent, such as an active ester of 4-(tri-n-butyl)benzoic acid. The modified oligonucleotide ha
