21560-29-2Relevant articles and documents
NHC-Organocatalyzed CAr?O Bond Cleavage: Mild Access to 2-Hydroxybenzophenones
Janssen-Müller, Daniel,Singha, Santanu,Lied, Fabian,Gottschalk, Karin,Glorius, Frank
supporting information, p. 6276 - 6279 (2017/05/19)
A Truce–Smiles rearrangement of acyl-anion equivalents generated by N-heterocyclic carbene (NHC) catalysis has been achieved. The developed method includes CAr?O, CAr?S, or CAr?N bond cleavage for the formation of a CAr?C bond and enables access to 2-hydroxybenzophenones, an important structural motif that is present in several bioactive natural products. By utilizing this procedure, the alkaloid taxilamine was synthesized in three steps. DFT calculations and control experiments support a classical SNAr mechanism with a catalyst-bound Meisenheimer-type intermediate. The method features mild reaction conditions, excellent functional-group tolerance, and a broad substrate scope, including various classes of (hetero)arenes.
Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists
Hu, Yun-Jin,St.-Onge, Miguel,Laliberté, Sébastien,Vallée, Frédéric,Jin, Shujuan,Bedard, Leanne,Labrecque, Jean,Albert, Jeffrey S.
supporting information, p. 3199 - 3203 (2014/06/24)
A series of TRPA1 antagonists is described having a 4-aryloxy-1H-pyrrolo[3, 2-c]pyridine or a 1-aryloxyisoquinoline scaffold. These compounds have high ligand efficiency and favorable physical properties and may thus serve as scaffolds for further optimization.
NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING-II; GRIGNARD COUPLING OF HETEROCYCLIC COMPOUNDS
Tamao, K.,Kodama, S.,Nakajima, I.,Kumada, M.,Minato, A.,Suzuki, K.
, p. 3347 - 3354 (2007/10/02)
A general, versatile method for alkylation and arylation of haloheterocyclic compounds is reported.In the presence of a catalytic quantity of , where dppp stands for Ph2P(CH2)3PPh2, bromothiophenes, halopyridines, haloquinoline, and haloisoquinolines reacted with alkyl and aryl Grignard reagents at room temperature or at ether refluxing temperature to give the cross-coupling products.The coupling reactions has been applied to the synthesis of isoquinoline alkaloids.Reactivities of 2-thienyl and 2-pyridyl Grignard reagents have also been examined.