Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin.
[reaction: see text] Atom transfer carbonylation (ATC) of alkyl iodides leading to carboxylic acid esters is effectively accelerated by Pd(PPh(3))(4) and Mn(2)(CO)(10) under photoirradiation conditions. In the presence of amines, Pd(0) complexes affected double carbonylations leading to alpha-keto amides, whereas Mn(2)(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.
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
Takahide
T
Fukuyama
Satoshi
S
Nishitani
Takaya
T
Inouye
Keisuke
K
Morimoto
Ilhyong
I
Ryu
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000480:Alkynes / Q000737:chemistry; D052117:Benzodioxoles; D002211:Capsaicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004149:Dioxoles / Q000138:chemical synthesis*; D007454:Iodides / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis*; D017895:Manganese Compounds / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
D000480:Alkynes; D052117:Benzodioxoles; D004149:Dioxoles; D007454:Iodides; D017705:Lignans; D017895:Manganese Compounds; C475934:hinokinin; D010165:Palladium; D015107:4-Butyrolactone; D002211:Capsaicin; C012906:dihydrocapsaicin