[読みたい論文] 添加剤不要!パラジウム触媒下でのビアリール合成

Viewed: 19:37:01 in December 11, 2019

Posted: July 5, 2019

Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides (Daley, Ryan A.; Liu, En-Chih; Topczewski, Joseph J.)
Org. Lett. 2019, 21 (12), 4734−4738.

Keywords: Pd; Xphos; cod; 1,4-dioxane


Pd触媒下での安息香酸化合物と塩化アリールのカップリングについて報告しているようです。脱炭酸が起こり、ビアリールが生成する模様。

Pd触媒によるビアリール生成に通常必要な添加剤、例えばちょっと反応の毛色が違いますがSuzuki−Miyauraカップリングでは塩基が必要だったりするのですが、そういうのが要らないというのがこの論文の売りということらしいです。ただ、基質が安息香酸ナトリウムというのはちょっとずるいかな。

とはいえ一応添加剤不要ということで、シンプルな反応系を目指しているというのは要旨から読み取れます。できればPd触媒もスポンジとかにすればよかったんじゃないかなとは思いましたが、反応条件の最適化の結果、PdソースがPd(cod)(CH2SiMe3)2、そして配位子にXphosを添加しているあたり、簡単に進む反応ではないのかもしれません。反応温度も140℃とかより高温とかですし。脱炭酸がしんどいのかな。

カルボン酸塩のチョイスがちょっと謎なので、読みたい論文に追加です。

Supporting Informationを見たのですが、この脱炭酸反応、閉鎖系で行なっているのでしょうか…。

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。

 

2015年はこんな年

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DNA修復の仕組みの研究
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できごと
スイス・フランの対ユーロの上限、1ユーロ=1.20フランを廃止
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戦艦武蔵をシブヤン海海底で発見
姫路城天守閣の一般公開を再開
広島空港に着陸しようとしたアシアナ航空機が滑走路から外れ停止
日本の超電導リニア車両が有人走行実験で時速603キロを記録
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室戸岬のネコ。

 

計算終わりました

 

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3Q
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7〜9月)。

 

[読みたい論文] 臭くないチオフェオール源をチオ尿素から作ります
昔チオフェノールの生で怒られたことあります。
Chem. Eur. J. 2019, 84 (37), 8903−8910.

描くのが大変なくらいでっかい環状ラクトンを作ります。
1箇所二重結合を入れとくのがいいのでしょうか。
J. Org. Chem. 2019, 84 (12), 8019−8026.

[読みたい論文] 金属触媒を使うことなく実質ヒドロホルミル化します
環状アセタールの水素をぶっこぬきます
Chem. Lett. 2019, 48 (7), 715−717.

金属触媒を使うことなくアルデヒドを脱カルボニル化させます
アタマと反応剤は使いよう
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Cu触媒によるgem-ジボリルアルカンのアミノ化反応
アミノ酸のカルボキシル基がホウ素になったやつ。
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アルキンにボリル基をふたつ導入します
モル比を知りたいところ。
Org. Lett. 2019, 21 (12), 4739−4744.

可視光酸化還元触媒でベンゼン環にカルボキシル基を導入します。
この論文にも努力と根性の跡が。
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可視光酸化還元触媒でベンゼン環やアルケンにカルボキシル基を導入します。
努力と根性の跡。
Org. Lett. 2019, 21 (12), 4486−4489.

[読みたい論文] 眼に優しそうなアルキンの臭化水素付加反応
反応剤は少なくとも3つに分解します。
Org. Lett. 2019, 21 (12), 4531−4534.

[読みたい論文] ニオブ触媒下で塩化アルキルをアルカンにします
ヒドロデハロゲネーション。
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注目のWebコンテンツ

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(有機化学を学ぶ人のブログ)
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https://yuukiwomanabu.com/2019...

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https://www.aori.u-tokyo.ac.jp...

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[J. Nat. Prod. 20190704025616, 2019, 6−1471]
Isolation of Sesquiterpene–Amino Acid Conjugates, Onopornoids A–D, and a Flavonoid Glucoside from Onopordum alexandrinum
(Sugimoto, Sachiko; Yamano, Yoshi; Desoukey, Samar Y.; Katakawa, Kazuaki; Wanas, Amira S.; Otsuka, Hideaki; Matsunami, Katsuyoshi)
Tag: 123-75-1

[J. Nat. Prod. 20190704025726, 2019, 6−1518]
Inhibitory Effects of Phenylpropanoid Derivatives from Oenanthe javanica on Antigen-Stimulated Degranulation in RBL-2H3 Cells
(Murata, Toshihiro; Katagiri, Tatsuo; Ishikawa, Yoshinobu; Abe, Mizuki; Takahashi, Emi; Iwahana, Ruka; Sakamoto, Yuko; Sasaki, Kenroh)
Tag: AC, Phg, Me

[J. Nat. Prod. 2019070402593, 2019, 6−1609]
Konamycins A and B and Rubromycins CA1 and CA2, Aromatic Polyketides from the Tunicate-Derived Streptomyces hyaluromycini MB-PO13T
(Harunari, Enjuro; Imada, Chiaki; Igarashi, Yasuhiro)
Tag: RSA, PK, C, R, SOD

[J. Nat. Prod. 20190704025928, 2019, 6−1634]
Bioactive Diterpenoids from the Stems of Euphorbia antiquorum
(Liang, Yue; An, Lijun; Shi, Zhaoyu; Zhang, Xuke; Xie, Chunfeng; Tuerhong, Muhetaer; Song, Zhaohui; Ohizumi, Yasushi; Lee, Dongho; Shuai, Ling; Xu, Jing; Guo, Yuanqiang)
Tag: LPS, NO, AC, CD

[J. Nat. Prod. 20190704025928, 2019, 6−1627]
Possible Biosynthetic Products and Metabolites of Kainic Acid from the Red Alga Digenea simplex and Their Biological Activity
(Maeno, Yukari; Terada, Ryuta; Kotaki, Yuichi; Cho, Yuko; Konoki, Keiichi; Yotsu-Yamashita, Mari)
Tag: LGA, E, Glu, R, AC, DMA, 123-75-1

[J. Nat. Prod. 20190704025948, 2019, 6−1656]
Isolation and Biological Activity of 8-Epitetrodotoxin and the Structure of a Possible Biosynthetic Shunt Product of Tetrodotoxin, Cep-226A, from the Newt Cynops ensicauda popei
(Kudo, Yuta; Yotsu-Yamashita, Mari)
Tag: Na, TTX

[Chem. Soc. Rev. 20190704030722, 2019, 13−3613]
Small molecule activation by boron-containing heterocycles
(Su, Yuanting; Kinjo, Rei)
Tag: B, Het