[読みたい論文] アリールメチルスルフィドからのアリールカルボン酸エステル合成

Viewed: 08:24:14 in December 9, 2019

Posted: April 25, 2019

Palladium-Catalyzed Alkoxycarbonylation of Arylsulfoniums (Minami, Hiroko; Nogi, Keisuke; Yorimitsu, Hideki)
Org. Lett. 2019, 21 (8), 2518−2522.

Keywords: Pd; Xantphos; iPr2NEt; MeOTf

スルホニウム塩の化学。炭素−硫黄結合をどう切断するかという問題に対する解決法の一つでもあります。


アリールメチルスルフィドとメチルメチルメチルトリフラートからスルホニウム塩を系中で発生させてパラジウム触媒の存在下で一酸化炭素とアルコールと反応させ、アリールカルボン酸エステルにするという内容のようです。

Graphical Abstract中のXantphosとは下の構造の通り2座のホスフィン。


反応条件の探索のための基質がメチルp-トリルスルフィドである理由は、NMRでの収率算出に都合がいいからだと思われます。

本文中で反応機構が提唱されていて、生成物が出来て行く経路については合理的かなと思うのですが、素朴な疑問として「なんでPdにくっつくのがメチル基じゃなくてアリール基なん?」というのあるんです。言い換えれば、酢酸エステルが生成しない理由は何か?と。ヨードニウム塩とかだとどっちが横でどっちが上でここが脱離しやすいとかいう話になるはずだけど、硫黄だとどうなるんでしょうね。

オープンアクセスなので読むことはできましたが、スルホニウム塩の構造などについても考えんといかんなと思ったので、(しっかりと)読みたい論文に追加です。

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。

 

1971年はこんな年

人名反応など
Abramov反応 [Doi 1]
Hajos−Parris−Eder−Sauer−Wiechert反応Kochiクロスカップリング [Doi 1]
Masamune−Bergman環化 [Doi 1] [Doi 2]
Minisci反応 [Doi 1]
Mizoroki−Heck反応 [Doi 1] [Doi 2]
Seyferth−Gilbert反応 [Doi 1] [Doi 2]
ノーベル化学賞
遊離基の電子構造と幾何学的構造の研究
(Gerhard Herzberg)
できごと
世界経済フォーラム(WEF)設立。ダボス会議。
アスワンダム公式開通
「新婚さんいらっしゃい!」放送開始(朝日放送)
「セキスイハイム」発売(積水化学工業)
NASDAQによる証券取引はじまる
多摩ニュータウンの入居が始まる
自動車などの6業種の資本自由化実施
「ゴールデン洋画劇場」放映開始(フジテレビ)
「仮面ライダー」放映開始
「non-no」創刊(集英社)
ノエビア設立
環境庁発足
マクドナルド銀座店オープン
プリンスホテル設立
ニクソン・ショック
円変動相場制移行
「サッポロ一番塩らーめん」発売(サンヨー食品)
「小枝」発売(森永製菓)
「カップヌードル」発売(日清食品)
第一勧業銀行発足
「マジックリン」発売(花王石鹸=花王)
「スター誕生!」放送開始(日本テレビ)
「テレビマガジン」創刊(講談社)
川崎ローム斜面崩壊実験事故
ソ連の火星探査機マルス2号が火星に衝突
スミソニアン体制発足

 

きょうのどうぶつ

ここの画像を使用しています。

ずぶ濡れの黒2号。

 

きょうの計算

 

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2Q
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4〜6月)。

 

[読みたい論文] 分子触媒でアルデヒドの端っこをメチレン化
ホルムアルデヒドを使います。
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金属使うと厄介だったんですよね。
ACS Omega 2019, 4 (4), 6690−6696.

各元素がどの分野で活発に研究されているかをまとめました
毎日更新できるように頑張ります。

[読みたい論文] フラストレイテットルイスペアで金錯体
ヒドロアミノ化の触媒にもなります。
Chem. Commun. 2019, 55 (30), 4367−4370.

[読みたい論文] アミドの反応性をNMRで予測します
じれねじれてケミカルシフト
Chem. Commun. 2019, 55 (30), 4423−4426.

[読みたい論文] マグネシウム錯体によるフルオロ炭素−アミノ化反応
実験操作に気になるところありです。
Chem. Commun. 2019, 55 (30), 4339−4342.

[読みたい論文] 脱水素を経るカルボニルα炭素−アルケニル炭素結合形成反応
第4周期の遷移金属触媒で初。
J. Am. Chem. Soc. 2019, 141 (14), 2298−2301.

[読みたい論文] 6員環遷移状態を経るヒドリド移動反応
立体選択的反応の基本です。
Org. Lett. 2019, 21 (7), 2298−2301.

[読みたい論文] ヨウ化アルキルと小員環アルキルマグネシウムのクロスカップリング
コバルト触媒下でのC−C結合形成反応です。
Org. Lett. 2019, 21 (7), 2285−2289.

[読みたい論文] スルホニルイミドでシクロプロパン化します。
ジアゾ化合物不要なのが売りのようです。
Org. Lett. 2019, 21 (7), 2265−2268.

 

注目のWebコンテンツ

引っ張ると白い蛍光を出すゴムの開発に成功〜材料が受けるダメージの可視化に期待〜
(北海道大学)
https://www.hokudai.ac.jp/news/2019/04/post-525.html

スペインバルセロナのHarbour.Space University とは?
(論文博士を取得した企業研究者のブログ)
https://researcher-gakui.com/post-1527/

東大、窒素ガスと水からのアンモニア合成に成功
(日本経済新聞)
https://www.nikkei.com/article/DGXLRSP507794_W9A410C1000000/

哺乳類内在色素・ビリベルジンを結合する分子の合理的設計と応用利用
(東京大学)
https://www.u-tokyo.ac.jp/focus/ja/press/z0109_00143.html

室温で緑色発光するp型/n型新半導体を独自の化学設計指針をもとにペロブスカイト型硫化物で実現
(Chem-Station)
https://www.chem-station.com/blog/2019/04/pn.html

巨大原始星の周りにアルミニウムを含む分子を発見
(理化学研究所)
http://www.riken.jp/pr/press/2019/20190425_1/

機能性ペプチドによる巨大DNAの細胞内導入
(理化学研究所)
http://www.riken.jp/pr/press/2019/20190425_2/

フラストレート磁性体の量子相転移の圧力・磁場制御を実現
(東京工業大学)
https://www.titech.ac.jp/news/2019/044188.html

多様なモノクロナル抗体分子を迅速に作製するペプチドバーコード手法を確立
(京都大学)
http://www.kyoto-u.ac.jp/ja/research/research_results/2019/190424_1.html

平成31年度科学技術分野の文部科学大臣表彰 5名の教員が受賞
(早稲田大学)
https://www.waseda.jp/inst/research/news/69727

 

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Tag: PIP, ppz

液晶  
[Org. Process Res. Dev. 20190424092812, 2019, 4−477]
Stereoselective Acetalization for the Synthesis of Liquid-Crystal Compounds Possessing a trans-2,5-Disubstituted 1,3-Dioxane Ring with Saturated Aqueous Solutions of Inorganic Salts
(Maebayashi, Haruki; Fuchigami, Tsugumichi; Gotoh, Yasuyuki; Inoue, Munenori)
Tag: DIOX, PDO, LC

[Org. Process Res. Dev. 20190424092950, 2019, 4−484]
Practical Preparation of a 1,3,5-Trisubstituted Pyridazin-4(1H)-one Using Selective C1 Unit Insertion and Cyclization
(Suzuki, Akihiro; Fukuda, Naohiro; Kajiwara, Takeshi; Ikemoto, Tomomi)
Tag: PDE, Ac, HPz, pzH, pz, 100-63-0, Ar

環化付加反応  
[Org. Process Res. Dev. 2019042409311, 2019, 4−493]
Self-Assembled Polymeric Pyridine Copper Catalysts for Huisgen Cycloaddition with Alkynes and Acetylene Gas: Application in Synthesis of Tazobactam
(Hu, Hao; Ohno, Aya; Sato, Takuma; Mase, Toshiaki; Uozumi, Yasuhiro; Yamada, Yoichi M. A.)
Tag: P4VP, Cu, Na, C2H2, pyr, Asc, VP, Py, C, CA, TON, Cat

[Org. Process Res. Dev. 20190424093139, 2019, 4−499]
Process Development of an Efficient and Cost-Effective Telescoping Route to a Key Synthetic Precursor for the Preparation of a Renin Inhibitor
(Nonoyama, Akihito; Nakai, Yoshio; Lee, Shoukou; Suzuki, Satoshi; Ando, Takeya; Fukuda, Nobuhisa; Tanaka, Hiroaki; Takahashi, Kazuhiko)

[Org. Process Res. Dev. 20190424093253, 2019, 4−512]
Improved Manufacturing Route and Polymorphic Control of a Potent and Selective Anaplastic Lymphoma Kinase (ALK) Inhibitor ASP3026
(Takahama, Yuji; Obitsu, Kazuyoshi; Takeguchi, Kazuhiro; Hirasawa, Shun; Kobayashi, Koji; Akiba, Takahiro; Ueda, Norihiro; Orii, Ryoki; Ohigashi, Atsushi; Takahashi, Takumi; Okada, Minoru; Ieda, Shigeru)
Tag: RA, ALK, Nme, CC, PIP, ppz, Me

[Org. Process Res. Dev. 20190424093339, 2019, 4−524]
Development of an Efficient Manufacturing Process for a Key Intermediate in the Synthesis of Edoxaban
(Michida, Makoto; Ishikawa, Hideaki; Kaneda, Takeshi; Tatekabe, Shinya; Nakamura, Yoshitaka)
Tag: NGP, PFR

[Org. Process Res. Dev. 20190424093354, 2019, 4−535]
Construction of a (3aR,4R,9bR)-Hexahydropyrroloquinoline by Stereoselective Hydrogen-Mediated Domino Cyclization
(Yamada, Masatoshi; Usutani, Hirotsugu; Ito, Tatsuya; Yamano, Mitsuhisa)
Tag: HPLC, LC, H, as, Rh, C, Cat

環化付加反応  
[Org. Process Res. Dev. 2019042409348, 2019, 4−548]
Synthesis of Tofogliflozin as an SGLT2 Inhibitor via Construction of Dihydroisobenzofuran by Intramolecular [4 + 2] Cycloaddition
(Murakata, Masatoshi; Kawase, Akira; Kimura, Nobuaki; Ikeda, Takuma; Nagase, Masahiro; Koizumi, Masatoshi; Kuwata, Kazuaki; Maeda, Kenji; Shimizu, Hitoshi)
Tag: Glu, Na, Glc, Glu, Glu, CA

パラジウム  
[Org. Process Res. Dev. 20190424093423, 2019, 4−558]
Practical and Scalable Synthetic Method for Preparation of Dolutegravir Sodium: Improvement of a Synthetic Route for Large-Scale Synthesis
(Aoyama, Yasunori; Hakogi, Toshikazu; Fukui, Yuki; Yamada, Daisuke; Ooyama, Takao; Nishino, Yutaka; Shinomoto, Shoji; Nagai, Masahiko; Miyake, Naoki; Taoda, Yoshiyuki; Yoshida, Hiroshi; Yasukata, Tatsuro)
Tag: Pd, Na

[Org. Process Res. Dev. 20190424093437, 2019, 4−565]
Practical Synthetic Method for the Preparation of Pyrone Diesters: An Efficient Synthetic Route for the Synthesis of Dolutegravir Sodium
(Yasukata, Tatsuro; Masui, Moriyasu; Ikarashi, Fumiya; Okamoto, Kazuya; Kurita, Takanori; Nagai, Masahiko; Sugata, Yoshihide; Miyake, Naoki; Hara, Shinichiro; Adachi, You; Sumino, Yukihito)
Tag: Na

[Org. Process Res. Dev. 20190424093451, 2019, 4−571]
Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NOx Catalysis: Large-Scale Preparation of Shi’s Catalyst
(Sasano, Yusuke; Sato, Hikaru; Tadokoro, Shinsuke; Kozawa, Masami; Iwabuchi, Yoshiharu)
Tag: AA, as, C, AcOH

触媒的芳香族求核置換 芳香族求核置換  
[Org. Process Res. Dev. 2019042409356, 2019, 4−578]
Scalable Process Design for a PDE10A Inhibitor Consisting of Pyrazolopyrimidine and Quinoxaline as Key Units
(Yamagami, Takafumi; Kobayashi, Ryo; Moriyama, Noriaki; Horiuchi, Hideki; Toyofuku, Eiji; Kadoh, Yoichi; Kawanishi, Eiji; Izumoto, Shinichi; Hiramatsu, Hajime; Nanjo, Takehiro; Sugino, Masuhiro; Utsugi, Masayuki; Moritani, Yasunori)
Tag: 141-82-2, EWG, Nu, 91-19-0, NAS, e-, SNAr

[Org. Process Res. Dev. 2019042409358, 2019, 4−588]
Ammonium Salt-Accelerated Hydrazinolysis of Unactivated Amides: Mechanistic Investigation and Application to a Microwave Flow Process
(Noshita, Megumi; Shimizu, Yuhei; Morimoto, Hiroyuki; Akai, Shuji; Hamashima, Yoshitaka; Ohneda, Noriyuki; Odajima, Hiromichi; Ohshima, Takashi)
Tag: am, NH2, 302-01-2

[Org. Process Res. Dev. 20190424093515, 2019, 4−595]
Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives
(Asakawa, Tomohiro; Sagara, Hiroto; Kanakogi, Masaki; Hiza, Aiki; Tsukaguchi, Yuta; Ogawa, Takahiro; Nakayama, Miho; Ouchi, Hitoshi; Inai, Makoto; Kan, Toshiyuki)
Tag: PKG, PKA

[Org. Process Res. Dev. 20190424093517, 2019, 4−603]
Development of an Efficient Manufacturing Process for E2212 toward Rapid Clinical Introduction
(Isomura, Minetaka; Nakamura, Taiju; Kamada, Atsushi; Sasaki, Takeo; Uemura, Toshiyuki; Hoshino, Yorihisa; Matsuda, Masaaki; Hu, Yongbo; Hasegawa, Daiju; Inanaga, Kazato; Sato, Nobuaki; Yoshizawa, Kazuhiro; Moniz, George A.; Wilkie, Gordon D.; Fang, Francis G.; Nishikawa, Yoshihiro; Tagami, Katsuya)

[Org. Process Res. Dev. 20190424093524, 2019, 4−614]
Regioselective Formylation of Pyrrole-2-Carboxylate: Crystalline Vilsmeier Reagent vs Dichloromethyl Alkyl Ether
(Warashina, Takuya; Matsuura, Daisuke; Sengoku, Tetsuya; Takahashi, Masaki; Yoda, Hidemi; Kimura, Yoshikazu)
Tag: For, Pr, Bu, PY, Alk

不斉合成  
[Org. Process Res. Dev. 20190424093532, 2019, 4−619]
Large Scale Synthesis of Chiral (3Z,5Z)-2,7-Dihydro-1H-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids
(Takahashi, Motohiro; Moriwaki, Hiroki; Miwa, Toshio; Hoang, Brittanie; Wang, Peng; Soloshonok, Vadim A.)
Tag: AA, as, G, Gly, SB, AS

不斉合成  
[Org. Process Res. Dev. 20190424093537, 2019, 4−629]
Expedient Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid via Alkylation of Chiral Nucleophilic Glycine Equivalent
(Mei, Haibo; Hiramatsu, Takahiro; Takeda, Ryosuke; Moriwaki, Hiroki; Abe, Hidenori; Han, Jianlin; Soloshonok, Vadim A.)
Tag: as, G, Gly, Nu, AS

[Org. Process Res. Dev. 20190424093544, 2019, 4−635]
Molecular Weight Distribution of Polymers Produced by Anionic Polymerization Enables Mixability Evaluation
(Endo, Yuta; Furusawa, Mai; Shimazaki, Toshiya; Takahashi, Yusuke; Nakahara, Yuichi; Nagaki, Aiichiro)
Tag: St, MWD

イオン液体  
[Org. Process Res. Dev. 20190424093559, 2019, 4−641]
Modeling and Design of a Flow-Microreactor-Based Process for Synthesizing Ionic Liquids
(Nakahara, Yuichi; Metten, Bert; Tonomura, Osamu; Nagaki, Aiichiro; Hasebe, Shinji; Yoshida, Jun-ichi)
Tag: BMImCl, Bu, BDMIM, CFD, BMIM, IL, RLS

[Org. Process Res. Dev. 20190424093615, 2019, 4−648]
H–D Exchange Deuteration of Arenes at Room Temperature
(Sawama, Yoshinari; Nakano, Akihiro; Matsuda, Takumi; Kawajiri, Takahiro; Yamada, Tsuyoshi; Sajiki, Hironao)
Tag: Ir, C, H, Pt, PrOH, PA, F, PGM, PhOH, C

[Org. Process Res. Dev. 20190424093630, 2019, 4−654]
Efficient and Practical Deacylation Reaction System in a Continuous Packed-Bed Reactor
(Yasukouchi, Hiroaki; Machida, Koji; Nishiyama, Akira; Mitsuda, Masaru)
Tag: AER, PBR, C

[Org. Process Res. Dev. 20190424093648, 2019, 4−660]
Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
(Yamamoto, Kosuke; Ishimaru, Shota; Oyama, Tatsuya; Tanigawa, Satoko; Kuriyama, Masami; Onomura, Osamu)
Tag: NBS, Cu, Ser, S, C, Ar

[Org. Process Res. Dev. 2019042409373, 2019, 4−667]
Improved Synthesis of Unsymmetrical Carbonate Derivatives Using Calcium Salts
(Hamada, Tomohito; Okada, Michiaki; Yamauchi, Akiyoshi; Kishikawa, Yosuke)
Tag: Ca, Ca(OH)2