[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

Viewed: 05:04:19 in December 11, 2019

Posted: July 4, 2019

Synthesis of Air-stable, Odorless Thiophenol Surrogates via Ni-Catalyzed C−S Cross-Coupling (Magné, Valentin; Ball, Liam T.)
Chem. Eur. J. 2019, 84 (37), 8903−8910.

Keywords: Ni; thiourea; thiophenol; PCy3; 3,5-dinitrobenzoic acid


ニッケル触媒下でのヨウ化アリールとチオ尿素の反応を経るチオフェノール等価体の合成について報告しているようです。反応溶媒(?)は水の模様。ニッケルは2価の前駆体をピコリンボランで還元して0価にして使っています。

チオフェノールを取り扱った人なら経験があると思いますが、チオフェノール、めっちゃ臭いです、毒物指定に異議なしです。一方この論文で扱っているチオフェノール等価体、臭くないことが特徴のようですが、なんで臭くないかというと「塩」だからなんですよね。揮発性が全くないので空気中に漂わない。で、何の塩かというと、3,5-ジニトロ安息香酸の塩。なんでこんなのと組み合わせたのか気になるところです。

反応機構はよくある酸化的付加・アニオン交換・還元的脱離でぐるぐるなんだろうと想像できますが、塩基はいらないんでしょうか。その辺りが気になりますので、読みたい論文に追加です。

確かに開放系で臭わないかもしれませんが、直接鼻につけてしまった時には(しないけど)、やっぱり臭いんでしょうね。

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。

 

2014年はこんな年

人名反応など
Molander Ir/Ni光酸化還元デュアル触媒系 [Doi 1]
ノーベル化学賞
超高解像度蛍光顕微鏡の開発
(Eric Betzig, Stefan Hell, William E. Moerner)
できごと
西アフリカ エボラ出血熱流行
千葉市で積雪33cm
イキケ地震(M8.2)
甲府市で積雪114cm
「マウントゴックス」ウェブサイトがアクセス不能
STAP細胞騒動
「あべのハルカス」完成
「森田一義アワー 笑っていいとも!」放送終了
「超高速!参勤交代」公開
「思い出のマーニー」公開
「台風の基準」を理由とする初の特別警報発表
広島市北部で大規模土砂災害
「ダメよ〜ダメダメ」
大韓航空ナッツ・リターン
小惑星探査機「はやぶさ2」打ち上げ

 

きょうのどうぶつ

ここの画像を使用しています。

ウツボの唐揚げは作りたてが良い。

 

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)。

 

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
Chem. Eur. J. 2019, 25 (36), 8508−8512.

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。
Org. Lett. 2019, 21 (12), 4759−4762.

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。
Org. Lett. 2019, 21 (12), 4632−4637.

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。
Chem. Commun. 2019, 55 (50), 7247−7250.

[読みたい論文] ジメトキシシランのどっちかのメトキシ基の方と反応します。
不斉中心のあるリチウムとの反応です。
Chem. Commun. 2019, 55 (48), 6882−6885.

 

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Tag: ET, C3H6, e-

[Angew. Chem. Int. Ed. 20190703095419, 2019, 27−9150]
Cooperative Catalysis of an Alcohol Dehydrogenase and Rhodium-Modified Periodic Mesoporous Organosilica
(Himiyama, Tomoki; Waki, Minoru; Maegawa, Yoshifumi; Inagaki, Shinji)
Tag: ADH, HLADH, PMO, AA, as, SA, LADH, Ph, BSA, Rh, C, Cat

[Angew. Chem. Int. Ed. 20190703095613, 2019, 27−9109]
Highly Reproducible Formation of a Polymer Single-Molecule Junction for a Well-Defined Current Signal
(Harashima, Takanori; Hasegawa, Yusuke; Kaneko, Satoshi; Kiguchi, Manabu; Ono, Tomoya; Nishino, Tomoaki)
Tag: ALGM, SM, BB, M

[Angew. Chem. Int. Ed. 2019070309596, 2019, 27−9022]
Near-Infrared-Emitting Nitrogen-Doped Nanographenes
(Yamato, Kairi; Sekiya, Ryo; Suzuki, Kaho; Haino, Takeharu)
Tag: TD, N, PL, ABS, FG, NIR, HLG, IR

[Angew. Chem. Int. Ed. 20190703095937, 2019, 27−8978]
Platforms for Stable Carbon-Centered Radicals
(Kato, Kenichi; Osuka, Atsuhiro)
Tag: C, R, O, e-

パラジウム  
[Chem. Eur. J. 20190703100129, 2019, 35−8387]
Synthesis of All Stereoisomers of Monomeric Spectomycin A1/A2 and Evaluation of Their Protein SUMOylation-Inhibitory Activity
(Nomura, Yusaku; Thuaud, FrÃdÃric; Sekine, Daisuke; Ito, Akihiro; Maeda, Satoko; Koshino, Hiroyuki; Hashizume, Daisuke; Muranaka, Atsuya; Cruchter, Thomas; Uchiyama, Masanobu; Ichikawa, Satoshi; Matsuda, Akira; Yoshida, Minoru; Hirai, Go; Sodeoka, Mikiko)
Tag: Pd, Al, Bn, CD, M

[Chem. Eur. J. 20190703100143, 2019, 35−8363]
Alkylative Carboxylation of Ynamides and Allenamides with Functionalized Alkylzinc Halides and Carbon Dioxide by a Copper Catalyst
(Takimoto, Masanori; Gholap, Sandeep Suryabhan; Hou, Zhaomin)
Tag: Cu, C, CO2, DB, FG-R, COOH, FG, Nu, C, Alk

[Chem. Eur. J. 20190703100430, 2019, 35−8268]
Impact of Group?10 Metals on the Solvent-Induced Disproportionation of o-Semiquinonato Complexes
(Yamada, Shota; Matsumoto, Takeshi; Chang, Ho-Chol)
Tag: Ni, tBu, t-Bu, Bu, PhMe, TolH, M

[Chem. Eur. J. 20190703100722, 2019, 35−8219]
Alloyed Tetranuclear Metal Chains of Pd4−nPtn (n=0?3) Scaffolded by a New Linear Tetraphosphine Containing a PNP Bridge
(Tanase, Tomoaki; Tanaka, Miho; Hamada, Mami; Morita, Yuka; Nakamae, Kanako; Ura, Yasuyuki; Nakajima, Takayuki)
Tag: ES, XR, ABS, XRD, e-

[Chem. Eur. J. 20190703101217, 2019, 36−8528]
Total Synthesis, Stereochemical Revision, and Biological Assessment of Iriomoteolide-2a
(Sakamoto, Keita; Hakamata, Akihiro; Iwasaki, Arihiro; Suenaga, Kiyotake; Tsuda, Masashi; Fuwa, Haruhiko)
Tag: SMC, AC, RCM

[Chem. Eur. J. 20190703101241, 2019, 36−8522]
Precise Proton Mapping near Ionic Micellar Membranes with Fluorescent Photoinduced-Electron-Transfer Sensors
(Uchiyama, Seiichi; Yano, Kayo; Fukatsu, Eiko; de?Silva, A. Prasanna)
Tag: ET, H, PET, PIET, BF, e-, HB

自己集合  
[Chem. Eur. J. 20190703101412, 2019, 36−8479]
Self-Assembly of Macrocyclic Boronic Esters Bearing Tellurophene Moieties and Their Guest-Responsive Phosphorescence
(Takahashi, Kohei; Shimo, Shunsuke; Hupf, Emanuel; Ochiai, Junichi; Braun, Christina A.; Torres?Delgado, William; Xu, Letian; He, Gang; Rivard, Eric; Iwasawa, Nobuharu)
Tag: B, SA, e-

[Eur. J. Inorg. Chem. 20190703101613, 2019, 24−2912]
The XB(C6F5)2 Halogenoborane Route to Phosphole Derivatives
(MÃricke, Jennifer; Ueno, Atsushi; Wibbeling, Birgit; Daniliuc, Constantin G.; Kehr, Gerald; Erker, Gerhard)

[Eur. J. Inorg. Chem. 20190703101613, 2019, 24−2918]
Salt of Ring-Reduced Iron(II) Octaethyltetrapyrazinoporphyrazine Containing Trimetallic Dianions with Peripherally Coordinated ZnCl2 Units: {FeII(TPyzPzEt8)4?(ZnCl2)2}2?
(Faraonov, Maxim A.; Romanenko, Nikita R.; Kuzmin, Alexey V.; Konarev, Dmitri V.; Shestakov, Alexander F.; Stuzhin, Pavel A.; Khasanov, Salavat S.; Otsuka, Akihiro; Yamochi, Hideki; Kitagawa, Hiroshi; Lyubovskaya, Rimma N.)
Tag: Zn, N, EA, pyz, Pc, Pht, e-

[Eur. J. Inorg. Chem. 20190703101649, 2019, 24−2891]
Oxido-Hydroxido- and Oxido-Aminato-Osmium(V) Complexes with a Cyclohexanediamine-Based Tetradentate Ligand as Active Oxidants for Dihydroxylation and Aminohydroxylation of Alkenes
(Fujimoto, Tomohiro; Sugimoto, Hideki; Kai, Kenichiro; Maeda, Kazuki; Itoh, Shinobu)
Tag: Os, chxn, St, CT, H, O, HP, H2O2, Cat

環化付加反応  
[Eur. J. Org. Chem. 20190703101926, 2019, 24−3916]
One-Pot Synthesis of Cycloocta[b]indole Through Formal [5+3] Cycloaddition Using Donor–Acceptor Cyclopropanes
(Okabe, Akito; Harada, Shinji; Takeda, Takuya; Nishida, Atsushi)
Tag: C, IND, LA, C3H6, C, CA

[Eur. J. Org. Chem. 20190703102017, 2019, 24−3882]
2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of Î-Keto Esters with Nitroolefins
(Togashi, Rei; Chennapuram, Madhu; Seki, Chigusa; Okuyama, Yuko; Kwon, Eunsang; Uwai, Koji; Tokiwa, Michio; Takeshita, Mitsuhiro; Nakano, Hiroto)
Tag: as, MR, C

[J. Polym. Sci. Part B: Polym. Phys. 20190703102237, 2019, 13−867]
Effects of water nanochannel diameter on proton transport in proton-exchange membranes
(Mabuchi, Takuya; Tokumasu, Takashi)
Tag: PEM, MDS, MD, RMD

[J. Polym. Sci. Part B: Polym. Phys. 20190703102412, 2019, 13−813]
Size and shape of Nafion particles in water after high-temperature treatment
(Yamaguchi, Makoto; Terao, Takeshi; Ohira, Akihiro; Hasegawa, Naoki; Shinohara, Kazuhiko)
Tag: PEM, SEC, PEMFC, PEFC, FC, EM, CL, Nf, cryo-TEM, TEM, e-, C

イオン液体 固体電池  
[ChemSusChem 20190703103026, 2019, 12−2637]
Rational Design of a Composite Electrode to Realize a High-Performance All-Solid-State Battery
(Kim, KyungSu; Park, Jesik; Jeong, Goojin; Yu, Ji-Sang; Kim, Yong-Chan; Park, Min-Sik; Cho, Woosuk; Kanno, Ryoji)
Tag: BTI, SE, Li, SS, Nme, NTf2, IL, SSB, Me, ASSB, SIC

[ChemSusChem 2019070310324, 2019, 12−2576]
Soluble Cello-Oligosaccharides Produced by Carbon-Catalyzed Hydrolysis of Cellulose
(Chen, Pengru; Shrotri, Abhijit; Fukuoka, Atsushi)
Tag: Glu, C, Glc, Glu, Glu, C