90843-22-4Relevant articles and documents
Palladium-catalyzed: Ortho -halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids
Ram, Shankar,Sharma, Ajay Kumar,Chauhan, Arvind Singh,Das, Pralay
, p. 10674 - 10677 (2020/10/02)
The 2-vinylbenzoic acids have wide applications in the field of polymer chemistry and are key precursors for the synthesis of important bioactive molecules. Herein, an ortho-halogen-induced deoxygenative approach for the generation of 2-vinylbenzoic acids from alkyl aryl ketones by palladium catalysis is discovered and explored. This approach requires no base or stoichiometric additives and can be carried out through a simple one-step process. Furthermore, the present reaction is scalable up to one-gram scale. The commercially available palladium on carbon (5 wt%) was used as a heterogeneous catalyst and showed excellent recyclability (5 times) without significant loss in catalytic activity. Pleasingly, under our optimized conditions, the alpha alkyl substituted 2-iodoacetophenones exhibit good diastereoselectivity and predominantly (E)-2-vinylbenzoic acids were obtained with good to excellent yields.
Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O-Benzoylhydroxylamines
Hemric, Brett N.,Shen, Kun,Wang, Qiu
supporting information, p. 5813 - 5816 (2016/06/09)
A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate sco
C3-symmetric cinchonine-squaramide-catalyzed asymmetric chlorolactonization of styrene-type carboxylic acids with 1,3-dichloro-5,5- dimethylhydantoin: An efficient method to chiral isochroman-1-ones
Han, Xin,Dong, Chune,Zhou, Hai-Bing
supporting information, p. 1275 - 1280 (2014/05/06)
A more practical and efficient catalytic asymmetric chlorolactonization of styrene-type carboxylic acids with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using C3-symmetric cinchonine-squaramide (CSCS) as organocatalyst has been developed. A series of chiral chloro-substituted isochroman-1-ones was obtained in excellent yields (up to 95%) and enantioselectivities (up to 99% ee), whwereby the results for chloro-substituted isochroman-1-ones are the best ever achieved. The catalyst can be recovered and reused for six cycles. Moreover, the chlorolactonization product 3b was further transformed to optically active bicyclic isochroman-1-one derivatives in high yield without losing the enantioselectivity. Furthermore, compounds 3e and 2n proved to be highly potent inhibitors of the HIV-1 in TZM-bl cells.