19832-98-5Relevant articles and documents
Silver-catalyzed decarboxylative C–H functionalization of cyclic aldimines with aliphatic carboxylic acids
Wang, Jingjing,Liu, Xue,Wu, Ziyan,Li, Feng,Qin, Tingting,Zhang, Siyuan,Kong, Weiguang,Liu, Lantao
, p. 2777 - 2781 (2021)
Silver-catalyzed decarboxylative C–H alkylation of cyclic aldimines with abundant aliphatic carboxylic acids has been realized under mild reaction conditions generating the corresponding products in moderate to good yields (32%–91%). In addition, a gram-scale reaction, late-stage modification of drug, synthetic transformation of the product, and further application of the catalytic strategy were also performed. Preliminary studies indicate that the reaction undergoes a radical process.
Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
Tan, Xinqiang,Liu, Zhonglin,Shen, Haigen,Zhang, Pei,Zhang, Zhenzhen,Li, Chaozhong
supporting information, p. 12430 - 12433 (2017/09/25)
The silver-catalyzed decarboxylative trifluoromethylation of aliphatic carboxylic acids is described. With AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of aliphatic carboxylic acids with (bpy)C
Catalytic activation of carbon-carbon bonds in cyclopentanones
Xia, Ying,Lu, Gang,Liu, Peng,Dong, Guangbin
, p. 546 - 550 (2017/04/01)
In the chemical industry, molecules of interest are based primarily on carbon skeletons. When synthesizing such molecules, the activation of carbon-carbon single bonds (C-C bonds) in simple substrates is strategically important: it offers a way of disconnecting such inert bonds, forming more active linkages (for example, between carbon and a transition metal) and eventually producing more versatile scaffolds. The challenge in achieving such activation is the kinetic inertness of C-C bonds and the relative weakness of newly formed carbon-metal bonds. The most common tactic starts with a three- or four-membered carbon-ring system, in which strain release provides a crucial thermodynamic driving force. However, broadly useful methods that are based on catalytic activation of unstrained C-C bonds have proven elusive, because the cleavage process is much less energetically favourable. Here we report a general approach to the catalytic activation of C-C bonds in simple cyclopentanones and some cyclohexanones. The key to our success is the combination of a rhodium pre-catalyst, an N-heterocyclic carbene ligand and an amino-pyridine co-catalyst. When an aryl group is present in the C3 position of cyclopentanone, the less strained C-C bond can be activated; this is followed by activation of a carbon-hydrogen bond in the aryl group, leading to efficient synthesis of functionalized α-tetralones - a common structural motif and versatile building block in organic synthesis. Furthermore, this method can substantially enhance the efficiency of the enantioselective synthesis of some natural products of terpenoids. Density functional theory calculations reveal a mechanism involving an intriguing rhodium-bridged bicyclic intermediate.
