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KAKEN_17K19126seika.pdf
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鉄触媒による不活性炭素-水素結合切断を経る官能基導入法の開発
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テツ ショクバイ ニ ヨル フカッセイ タンソ-スイソ ケツゴウ セツダン オ ヘル カンノウキ ドウニュウホウ ノ カイハツ
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Tetsu shokubai ni yoru fukassei tanso-suiso ketsugō setsudan o heru kannōki dōnyūhō no kaihatsu
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Developments of new methods of catalytic functionalization of unreactive C-H bonds using an iron complex
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垣内, 史敏
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カキウチ, フミトシ
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Kakiuchi, Fumitoshi
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慶應義塾大学・理工学部 (矢上) ・教授
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Research team head
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科研費研究者番号 : 70252591
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2020
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科学研究費補助金研究成果報告書
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2019
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本研究では、低原子価鉄錯体を触媒に用いる不活性炭素-水素結合を利用する直截的合成法の開発を行った。低原子価鉄触媒は酸素に不安定なため、有機合成反応における触媒として利用される例はあまり多くなく、特に炭素-水素結合の官能基化に利用した例は少ない。本研究において、芳香族ケトンと2位に置換基をもつメチレンシクロプロパン類との反応を行うと、オルト位炭素-水素結合とシクロプロパン環の炭素-炭素結合という2種類の不活性な結合切断を経て炭素-炭素結合生成反応が進行する新規環境低負荷型高選択的分子変換反応を開発することができた。本反応は、ホモアリル基を炭素-水素結合の切断を経て導入する新手法である。
In this research, I have investigated developments of new catalytic coupling reaction of aromatic ketones with methylenecyclopropane (MCP) derivatives via cleavages of carbon-hydrogen and carbon-carbon bonds. Fe(PMe3)4 showed excellent catalytic activity for this coupling reaction. The reaction of pivalophenone with 2-phenyl-1-methylenecyclopropane (2-Ph-MCP) using Fe(PMe3)4 as a catalyst gave an ortho homoallylation product in low yield. Interestingly, however, the reaction using 4-trifluoromethylpivalophenone proceeded to give the corresponding homoallylation product in excellent yield. Benzophenone derivatives can be utilized in this reaction. Instead of 2-Ph-MCP, when the reaction was conducted using 2,2-diPh-MCP, the coupling reaction using pivalophenone took place smoothly to give the corresponding homoallylation product in high yield. To the best of our knowledge, this is the first example of the C-H homoallylation using methylenecyclopropanes via C-H and C-C bond cleavages.
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研究種目 : 挑戦的研究 (萌芽)
研究期間 : 2017～2019
課題番号 : 17K19126
研究分野 : 有機合成化学
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