37985-07-2Relevant academic research and scientific papers
Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation
Zhang, Yu-Lan,Yang, Lei,Wu, Jie,Zhu, Chunyin,Wang, Peng
, p. 7768 - 7772 (2020/10/09)
Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl rad
Visible Light-Driven, Room Temperature Heck-Type Reaction of Alkyl Halides with Styrene Derivatives Catalyzed by B12 Complex
Chen, Li,Hisaeda, Yoshio,Shimakoshi, Hisashi
, p. 2877 - 2884 (2019/04/03)
A visible light driven Heck-type coupling reaction of alkyl halides with styrene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ru(bpy)3]Cl2 photosensitizer at room temperature is reported. The catalytic efficiencies of the B12 catalyst were compared to that of other cobalt complexes such as cobaloxime. Various control experiments supported a radical-based mechanism similar to those for typical B12 model reactions. A unique coupling reaction combined with 1,2-migration of the functional group is also reported. Mild reaction conditions using an environmentally benign cobalt catalyst derived from the natural B12 provided a practical protocol for the synthetic organic chemistry of the B12 catalyzed reaction system. (Figure presented.).
Borata-Wittig olefination reactions of ketones, carboxylic esters and amides with bis(pentafluorophenyl)borata-alkene reagents
Wang, Tongdao,Kohrt, Sonja,Daniliuc, Constantin G.,Kehr, Gerald,Erker, Gerhard
supporting information, p. 6223 - 6232 (2017/08/02)
The strongly electrophilic borane derivative amino-CH2CH2CH2-B(C6F5)26 was α-CH deprotonated with LiTMP to give the borata-alkene {[amino-(CH2)2-CHB(C6F5)2-][Li+]}29 which underwent facile [2 + 2] cycloaddition reactions with benzophenone or fluorenone to yield the respective 1,2-oxaboretanides 11a,b. Compounds 9 and 11 were characterized by the X-ray diffraction. Thermolysis or hydrolysis of compounds 11a,b gave the corresponding borata-Wittig olefination products 12a,b. A variety of R-CH2-CH2-B(C6F5)2 boranes (conveniently generated by hydroboration of terminal alkenes R-CHCH2 with Piers' borane [HB(C6F5)2]) were analogously deprotonated to give the respective borata-alkenes 16a-e (R: Ph-CH2-, nC4H9, tBu, Cy, PhCH2CH2-). They underwent "non-classical" borata-Wittig olefination reactions with ethylformate to give the respective enolether carbonylation products, or their C1-elongated aldehydes (after hydrolysis). The borata-alkene [Ph-(CH2)2-CHB(C6F5)2-] [Li+HTMP] (16a) gave the respective "non-classical" borata-Wittig olefination products, the enolethers 25a,b and 27, respectively, upon treatment with methyl- or ethyl acetate or γ-butyrolactone.
Stereocontrolled formation of styrenes by Pd(0)-catalyzed cross-coupling of photoactivated (E)-Alkenylgermanes with aryl bromides
Tseng, Chih-Chung,Li, Mungyuen,Mo, Bingli,Warren, Sarah A.,Spivey, Alan C.
supporting information; experimental part, p. 995 - 997 (2011/12/05)
The stereocontrolled synthesis of (E)-configured styrenes via Pd(0)-catalyzed cross-couping of (E)-alkenylgermanes with aryl bromides is described. The germanes employed have bis(naphthalen- 2-ylmethyl) substitution to allow photooxidative activation towa
