Novel Approaches for Carbonylation by the Cooperative Control of Radical and Metal Species

2014 Fiscal Year Final Research Report

• Project/Area Number: 23350045
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Osaka Prefecture University
• Principal Investigator: RYU Ilhyong 大阪府立大学, 理学(系)研究科(研究院), 教授 (80210821)
• Co-Investigator(Kenkyū-buntansha): FUKUYAMA Takahide 大阪府立大学, 理学系研究科, 准教授 (60332962) ; UEDA Mitsuhiro 大阪府立大学, 理学系研究科, 助教 (60566298)
• Project Period (FY): 2011-04-01 – 2015-03-31
• Keywords: ラジカル / カルボニル化 / 非対称ケトン / アシルリチウム / C-Hカルボニル化 / 光照射 / パラジウム

Outline of Final Research Achievements

Carbon monoxide is among important feedstock. In this study we have developed new carbonylation methods, which are based on the power of the strategy employing controlled dual species, such as radical and palladium species to achieve new carbonylation methods. Diesters were obtained in good yields by four-component coupling reactions comprising α-iodo esters, alkenes, CO, and alcohols under photo-irradiation conditions in the presence of Pd as a catalyst. Similarly the three-component reaction comprising α-iodo esters, CO, and amines gave good yields of β-keto amides with incorporation of CO. Unsymmetrical ketones, such as alkyl aryl ketones, were synthesized from iodoalkanes, CO and arylboronic acids in good yields. Polyoxodecatungstate anion was used as a photocatalyst to achieve a new type of C-H carbonylation reaction. Flow carbonylation was also examined successfully to affect high-yield trapping of CO by organolithium compounds.

Free Research Field

有機化学