有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
キレート形成を利用した不活性芳香族炭素結合切断を経る触媒的置換反応によるπ共役系拡張法の開発とその応用
河内 卓彌垣内 史敏
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ジャーナル 認証あり

2013 年 71 巻 6 号 p. 588-600

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Direct functionalization of unreactive bonds catalyzed by transition metal complexes has become a powerful tool in organic synthesis and has been studied extensively by many researchers. Our research group has been exploring regioselective functionalization via chelation-assisted cleavage of unreactive bonds by transition metal catalysts. Here we describe our recent efforts toward development of efficient methods for construction of π-conjugated systems by catalytic substitution via chelation-assisted cleavage of unreactive aromatic carbon-hydrogen and -heteroatom bonds. Ruthenium catalysts were employed to cleave aromatic carbon-hydrogen, carbon-oxygen, carbon-nitrogen, and carbon-fluorine bonds (aromatic carbon bonds) at ortho positions of directing groups and to introduce aryl, alkenyl, and carbonyl groups onto the aromatic rings. Application of these methods for short syntheses of substituted fused aromatic compounds such as twisted anthracenes, pentacenes, dibenzo[a,h]anthracenes, and picenes is also described.

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© 2013 社団法人 有機合成化学協会
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