34944-04-2Relevant academic research and scientific papers
Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source
Chen, Chen,Huang, Yujie,Ding, Jie,Liu, Liying,Zhu, Bolin
, p. 794 - 801 (2022/01/04)
We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.
Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO2
Chen, Xiao-Wang,Yue, Jun-Ping,Wang, Kuai,Gui, Yong-Yuan,Niu, Ya-Nan,Liu, Jie,Ran, Chuan-Kun,Kong, Wangqing,Zhou, Wen-Jun,Yu, Da-Gang
supporting information, p. 14068 - 14075 (2021/05/17)
Reductive carboxylation of organo (pseudo)halides with CO2 is a powerful method to provide carboxylic acids quickly. Notably, the catalytic reductive carbo-carboxylation of unsaturated hydrocarbons via CO2 fixation is a highly challenging but desirable approach for structurally diverse carboxylic acids. There are only a few reports and no examples of alkenes via transition metal catalysis. We report the first asymmetric reductive carbo-carboxylation of alkenes with CO2 via nickel catalysis. A variety of aryl (pseudo)halides, such as aryl bromides, aryl triflates and inert aryl chlorides of particular note, undergo the reaction smoothly to give important oxindole-3-acetic acid derivatives bearing a C3-quaternary stereocenter. This transformation features mild reaction conditions, wide substrate scope, facile scalability, good to excellent chemo-, regio- and enantioselectivities. The method highlights the formal synthesis of (?)-Esermethole, (?)-Physostigmine and (?)-Physovenine, and the total synthesis of (?)-Debromoflustramide B, (?)-Debromoflustramine B and (+)-Coixspirolactam A; thereby, opening an avenue for the total synthesis of chiral natural products with CO2.
Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source
Liu, Xianglei,Li, Bin,Gu, Zhenhua
, p. 7547 - 7554 (2015/08/18)
A palladium-catalyzed domino cyclization and carboxylation reaction for synthesis of a variety of carboxylic acids was developed, where chloroform was used as "carbon monoxide" source. The in situ generated neopentylpalladium species by Heck cyclization was efficiently trapped by dichlorocarbene to form a series of carboxylic acids. It was found that in this type of domino reaction CHCl3 is a convenient and safe alternation for CO gas.
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Suarez-Castillo, Oscar R.,Melendez-Rodriguez, Myriam,Castelan-Duarte, Luis Enrique,Sanchez-Zavala, Maricruz,Rivera-Becerril, Ernesto,Morales-Rios, Martha S.,Joseph-Nathan, Pedro
experimental part, p. 2374 - 2389 (2010/03/24)
We describe a reliable method for determining the absolute configuration of 2-(2-oxo-3-indolyl)acetamides based on analysis of the 1H NMR spectra of their phenylethylamide diastereomers. The conformational preferences for two diastereomeric ami
Palladium catalysed queuing processes. Part 1: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch and hydride, organotin(IV) or boron reagents
Brown, Stephen,Clarkson, Stephen,Grigg, Ronald,Thomas, W.Anthony,Sridharan, Visuvanathar,Wilson
, p. 1347 - 1359 (2007/10/03)
The concept of relay switch reactants, which substantially enhance the scope of our cyclization-anion capture methodology, is introduced and exemplified by a wide variety of catalytic cyclization-carbonylation-anion capture processes employing hydride, organostannanes and NaBPh4 as anion capture agents. Mono- and bis-cyclization processes forming 5- and 6-membered rings are described, all of which employ CO at atmospheric pressure. Cyclocarboformylation processes provide interesting analogues of hydroformylation.
