10385-09-8Relevant articles and documents
Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin
Fukuyama, Takahide,Nishitani, Satoshi,Inouye, Takaya,Morimoto, Keisuke,Ryu, Ilhyong
, p. 1383 - 1386 (2006)
Atom transfer carbonylation (ATC) of alkyl iodides leading to carboxylic acid esters is effectively accelerated by Pd(PPh3)4 and Mn2(CO)10 under photoirradiation conditions. In the presence of amines, Pd(0) complexes affected double carbonylations leading to α-keto amides, whereas Mn2(CO)10 accelerated only a single carbonylation reaction leading to the corresponding amides. The Pd(0)-accelerated ATC system was successfully applied to the synthesis of hinokinin and dihydrocapsaicin.
Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
Maulide, Nuno,Riomet, Margaux,Roller, Alexander,Zhang, Haoqi
supporting information, (2020/03/24)
Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
Pd/light-accelerated atom-transfer carbonylation of alkyl iodides: Applications in multicomponent coupling processes leading to functionalized carboxylic acid derivatives
Fusano, Akira,Sumino, Shuhei,Nishitani, Satoshi,Inouye, Takaya,Morimoto, Keisuke,Fukuyama, Takahide,Ryu, Ilhyong
supporting information; experimental part, p. 9415 - 9422 (2012/08/27)
The atom-transfer carbonylation reaction of various alkyl iodides thereby leading to carboxylic acid esters was effectively accelerated by the addition of transition-metal catalysts under photoirradiation conditions. By using a combined Pd/hv reaction system, vicinal C-functionalization of alkenes was attained in which α-substituted iodoalkanes, alkenes, carbon monoxide, and alcohols were coupled to give functionalized esters. When alkenyl alcohols were used as acceptor alkenes, three-component coupling reactions, which were accompanied by intramolecular esterification, proceeded to give lactones. Pd-dimer complex [Pd2(CNMe)6][PF6]2, which is known to undergo homolysis under photoirradiation conditions, worked quite well as a catalyst in these three- or four-component coupling reactions. In this metal/radical hybrid system, both Pd radicals and acyl radicals are key players and a stereochemical study confirmed the carbonylation step proceeded through a radical carbonylation mechanism. Light, camera, ATCion: Atom-transfer carbonylation of alkyl iodides to afford carboxylic acid esters was accelerated by the addition of transition-metal catalysts under photoirradiation. The carbonylation step proceeded through a radical mechanism. Copyright