448-53-3Relevant articles and documents
Scalable synthesis of oxazolones from propargylic alcohols through multistep palladium(II) catalysis: β-selective oxidative heck coupling of cyclic sulfonyl enamides and aryl boroxines
Alamsetti, Santosh Kumar,Persson, Andreas K. A.,Jiang, Tuo,Baeckvall, Jan-E.
, p. 13745 - 13750 (2013)
A whale of a scale: The title oxidative Heck coupling proceeded with unusual β selectivity to generate a variety of branched substituted oxazolones (see scheme; Ts=p-toluenesulfonyl). The three-step synthesis from readily available starting materials with a simple palladium catalyst and inexpensive reagents could be carried out in a single reaction vessel or scaled up for the preparation of large amounts of these amino acid precursors. Copyright
Rhodium-Catalyzed Enantioposition-Selective Hydroarylation of Divinylphosphine Oxides with Aryl Boroxines
Wang, Zhe,Hayashi, Tamio
supporting information, p. 1702 - 1706 (2018/02/06)
The rhodium-catalyzed hydroarylation of divinylphosphine oxides (RP(O)(CH=CH2)2) with aryl boroxines ((ArBO)3) gives the corresponding monoarylation products (RP(O)(CH=CHAr)CH2CH3) in high yields. One of the two vinyl groups in the phosphine oxide undergoes oxidative arylation while the other one is reduced to an ethyl moiety. These reactions proceed with high selectivity in terms of the enantiotopic vinyl groups in the presence of (R)-DTBM-segphos/Rh to give the P-stereogenic monoarylation products with high enantioselectivity.
Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines
Johnson, Thomas,Luo, Bo,Lautens, Mark
, p. 4923 - 4930 (2016/07/06)
We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57-91% yield and with greater than 92% ee in most cases.
Method for preparing 3-fluorine-2-aldehyde phenylboronic acid
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Paragraph 0014, (2017/02/09)
The invention discloses a method for preparing 3-fluorine-2-aldehyde phenylboronic acid. Starting from 3-fluorine phenylboronic acid, tripolymer is formed after heating reflux in methylbenzene or heptane and dehydration, then a lithium reagent is added to
Diastereoselective synthesis of vicinally bis(trifluoromethylated) alkylboron compounds through successive insertions of 2,2,2-trifluorodiazoethane
Molander, Gary A.,Ryu, Da Weon
supporting information, p. 14181 - 14185 (2015/02/19)
The usefulness of embedded CF3 substituents within organic substructures necessitates the development of diverse methods for incorporating this functional group. A recently reported route to α-trifluoromethylated alkylboron compounds by an α-transfer mechanism has now been extended to the synthesis of unprecedented, vicinally ditrifluoromethylated alkylboron compounds in a diastereoselective fashion. The utility of these products is highlighted by conversion of the C-B bond into other functional groups.
Nickel-catalyzed efficient and practical Suzuki-Miyaura coupling of alkenyl and aryl carbamates with aryl boroxines
Xu, Li,Li, Bi-Jie,Wu, Zhen-Hua,Lu, Xing-Yu,Guan, Bing-Tao,Wang, Bi-Qin,Zhao, Ke-Qing,Shi, Zhang-Jie
supporting information; experimental part, p. 884 - 887 (2010/04/29)
(Figure Presented) Suzuki-Miyaura coupling of unactivated alkenyl carbamates Is described to construct polysubstituted olefins. The developed process is also suitable for heteroaromatic and even electron-rich aromatic carbamates.
