68692-74-0Relevant academic research and scientific papers
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.
Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction
Shuler, Scott A.,Yin, Guoyin,Krause, Sarah B.,Vesper, Caroline M.,Watson, Donald A.
supporting information, p. 13830 - 13833 (2016/11/06)
The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.
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
A series of two oxidation reactions of ortho-alkenylbenzamide with hypervalent iodine(III): A concise entry into (3 R,4 R)-4-hydroxymellein and (3 R,4 R)-4-hydroxy-6-methoxymellein
Takesue, Takuya,Fujita, Morifumi,Sugimura, Takashi,Akutsu, Hiroki
supporting information, p. 4634 - 4637 (2015/01/09)
A sequence of oxidation reactions of alkenamides with hypervalent iodine is described. Oxidation of ortho-alkenylbenzamide substrates selectively gave isochroman-1-imine products. The products underwent further oxidation in the presence of a Pd salt catal
Supramolecular control of selectivity in hydroformylation of vinyl arenes: Easy access to valuable β-aldehyde intermediates
Dydio, Pawel,Reek, Joost N. H.
, p. 3878 - 3882 (2013/05/09)
Go against the flow! A rationally designed regioselective hydroformylation catalyst, [Rh/L], in which noncovalent ligand-substrate interactions allow the unprecedented reversal of selectivity from the typical α-aldehyde to the otherwise unfavored product β-aldehyde, is reported. This catalytic system opens up novel and sustainable synthetic pathways to important intermediates for the fine-chemicals industry.
Regioselective Pd-catalyzed aerobic aza-Wacker cyclization for preparation of isoindolinones and isoquinolin-1(2 H)-ones
Yang, Guoqiang,Zhang, Wanbin
supporting information; experimental part, p. 268 - 271 (2012/03/09)
A switchable regioselective intramolecular aerobic aza-Wacker cyclization catalyzed by palladium is presented. Isoindolinones or isoquinolin-1(2H)-ones could be prepared selectively from the same substrates using different catalysts. The type and steric hindrance of the ligands may be the variables most significant for regiocontrol.
Selenium-mediated synthesis of biaryls through rearrangement
Shahzad, Sohail A.,Vivant, Clotilde,Wirth, Thomas
supporting information; experimental part, p. 1364 - 1367 (2010/06/17)
"Chemical Equation Presented" A new cyclization of β-keto ester substituted stilbene derivatives using selenium electrophiles in the presence of Lewis acids is described. Substituted naphthols are obtained through cyclization and subsequent 1,2-rearrangement of aryl groups under very mild reaction conditions.
