[読みたい論文] 副反応を気にしなくて良いピナコールカップリング

Viewed: 13:41:35 in December 16, 2019

Posted: March 4, 2019

[J. Am. Chem. Soc. 2019, 141 (8), 3664−3669] Reductive Coupling between Aromatic Aldehydes and Ketones or Imines by Copper Catalysis (Takeda, Mitsutaka; Mitsui, Atsuhisa; Nagao, Kazunori; Ohmiya, Hirohisa)

Keywords: Cu; NHC; BPin; PhMe2SiBPin

銅触媒下でのケトンとアルデヒドのピナコールカップリングについて報告しているようです。ケトンの代わりにイミンを使うことによってアミノアルコールを合成することもできるのだとか。このテの反応は還元剤を必要とするのですがどれかなあとしばらく考えましたが、この記事の表題の化合物がそれでした。


このピナコールカップリング、ホモカップリング物の副生をうまく抑えたのが売りのようです。ホモカップリングの他、アルドール縮合も、ですね。


反応機構について詳しく知りたいので、読みたい論文に追加です。鍵となる反応中間体は下のようなもののようです。アルデヒドに対し優先的に(or アルデヒドに対してのみ)反応して、ケトンと反応していく、ということでしょうか。


この記事を書いた人
「牧岡ふうふ堂」オーナー。博士(工学)。
酒都圏在住。
某地方の国立系工業大学でアシスタントをしていました。 専門は有機反応・金属錯体(主に希土類)・π共役系。
twitterアカウントは@makiokafufudo(お仕事用)、@ymakioka(個人用)です。

 

きょうのどうぶつ

ここの画像を使用しています。

うちの庭を通り抜ける3匹の黒猫の中の1匹。朝青龍よりスリム。

 

あわせてどうぞ

SOHOのすすめ記事一覧 2019年
お仕事関係の記事のリストです(2019年)。

読みたい論文シリーズ − 2019年1Q
読みたいけと読んでいない論文を、構造式を描きながら紹介します(2019年1〜3月)。

 

[読みたい論文] 配位子の要らないPd触媒下でのアルケンの異性化
なぜタンタルなのでしょうか。
Chem. Commun. 2019, 55 (19), 2769−2772.

[読みたい論文] 水中での炭素−炭素結合形成反応に使えそうな有機ボロン酸アミド
水中でも分解しないボロン酸。
Chem. Commun. 2019, 55 (18), 2624−2627.

[化学系論文] Organometallicsでの日本人シェアを調べました−初巻から2018年の巻まで
ACS発行の有機金属化学系速報誌について調べました。

[読みたい論文] わざわざアミノボランを経由するアミンとアルデヒドからのイミン合成
アミノボランを経由する、アミンとアルデヒドからのアルジミン合成。
Angew. Chem. Int. Ed. 2019, 58 (9), 2875−2878.

[化学系論文] Org. Lett.での日本人シェアを調べました−初巻から2018年の巻まで
ACS発行の有機化学系速報誌について調べました。

[今日描いた構造式] 環状ホスホン酸3量体無水物
可逆的開環重合。
J. Am. Chem. Soc. 2019, 157 (7), 2894−2899.

[今日描いた構造式] hexamethylenecyclohexane
アレンのオリゴマー化。
Chem. Sci. 2019, 10 (8), 2478−2482.

[今日描いた構造式] (o‐borylaryl)phosphine
ホスフィンとピナコールボランから。
Angew. Chem. Int. Ed. 2019, 58 (9), 2850−2853.

[今日描いた構造式] 5-phenyl-1,2,3,4-thiatriazole
ニトリルとヒドラジンと硫黄と亜硝酸から。
Chem. Eur. J. 2019, 25 (10), 2457−2462.

[化学系論文] JOCでの日本人シェアを調べました−初巻から2018年の巻まで
JACSと比較することでちょっと見えてきたこととは?

 

注目の論文

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[Chem. Lett. 20190301113111, 2019, 3−230]
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パラジウム  
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[Chem. Commun. 20190301114738, 2019, 19−2749]
Stereogenic cyclic oligonaphthalenes displaying ring size-dependent handedness of circularly polarized luminescence (CPL)
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[J. Mater. Chem. C 2019030111552, 2019, 9−2577]
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カーボンナノチューブ  
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ナノ粒子  
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Tag: NS, EC

量子ドット  
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ナノ結晶 量子ドット  
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Tag: NR, XR, EM, Co, ND, QD, XRD, TEM, MIC, e-, TF