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KAKEN_23350047seika.pdf
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Title |
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二酸化炭素の資源化を指向する触媒的固定化反応の開発
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ニサンカ タンソ ノ シゲンカ オ シコウスル ショクバイテキ コテイカ ハンノウ ノ カイハツ
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Nisanka tanso no shigenka o shikosuru shokubaiteki koteika hanno no kaihatsu
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Research on CO2 incorporation reactions for synthetic organic chemistry
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山田, 徹
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ヤマダ, トオル
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Yamada, Toru
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慶應義塾大学・理工学部化学科・教授
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Research team head
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科研費研究者番号 : 40296752
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2015
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科学研究費補助金研究成果報告書
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2014
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銀触媒の存在下, 二酸化炭素がプロパルギルアルコールに導入され, 対応する環状カーボナートが得られる。本研究ではアルキン活性化を利用し炭素-炭素結合形成を伴う二酸化炭素固定化を試みた。アルキンを有するカルボニル化合物に塩基の存在下, 二酸化炭素と反応させると, 五員環ラクトンが得られた。この系をo-アルキニルアニリンに適用すると, アルキンに対しカルバミン酸アニオンが環化付加した, 対応するベンゾキサジン-2-オンが得られた。塩基にDBUを用いると, 4-ヒドロキシキノリン-2(1H)-オンが得られた。これは一次生成物に塩基が作用し, イソシアナート経由の分子内転位によることを赤外吸収スペクトルで確定した。
A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate from the reaction of CO2 with propargylic alcohols in high yields under mild conditions. We found that the catalytic amount of silver benzoate with MTBD was effective catalytic system and the corresponding lactone derivatives were obtained in high yields. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin at the activated C-C triple bond. In the presence of a catalytic amount of silver salt, various o-alkynylanilines were treated with carbon dioxide and DBU under mild reaction conditions to afford the corresponding 4-hydroxyquinolin-2(1H)-one derivatives in high yield. The key step is proposed as the generation of the isocyanate and the enolate through C-O bond cleavage and new C-C bond formation induced by deprotonation after formation of the benzoxazin-2-one.
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研究種目 : 基盤研究(B)
研究期間 : 2011~2014
課題番号 : 23350047
研究分野 : 有機化学
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