[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

Viewed: 19:37:45 in December 11, 2019

Posted: March 1, 2019

[Chem. Commun. 2019, 55 (19), 2769−2772] Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride (Murai, Masahito; Nishimura, Kengo; Takai, Kazuhiko)

Keywords: Pd

Pd/Ta触媒下での末端アルケンの異性化反応。おそらく熱力学的に最も安定な、芳香環に最も近い位置に炭素−炭素二重結合がある化合物が生成します。

この論文の売りは、配位子が不要であることなのでしょうか。確かに、反応後の後処理は楽なようです。


この反応で不思議なことの一つは、なぜTaCl5を共存させると望まれる反応が進行するのか、です。Supporing informationを眺めていると、TaCl5以外のものも検討しているようなのですが、それらの場合には副生成物が生成する模様。TaCl5が反応の中でどのような役割を果たしているのかは、本文を読まないとわからないようです。PdCl2のオリゴマー化を促進しているのであれば、イオン半径の似た金属塩化物を使用した場合や、他の金属塩化物の共存量を増やした場合にどうなるのか、知りたくなります。

もう一つ不思議なのは、PdCl2単独で反応を行った場合の、異性化生成物の比です。収率が1%未満の生成物、生成したとしても熱力学的にさらに安定な方へ異性化してしまうからこの数字なのだということなのでしょうか。また、上の反応例と関連して、メチレン鎖のより長い末端アルケンだとどうなるのか、気になるところです(反応例はあるようです)。


反応がシンプルな一方でわからないことも多く、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。

 

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Identification of the common biosynthetic gene cluster for both antimicrobial streptoaminals and antifungal 5-alkyl-1,2,3,4-tetrahydroquinolines
(Ozaki, Taro; Sugiyama, Ryosuke; Shimomura, Morito; Nishimura, Shinichi; Asamizu, Shumpei; Katsuyama, Yohei; Kakeya, Hideaki; Onaka, Hiroyasu)
Tag: KR, TE, THQ, OAc, A, PKS, PK, Alk, ACP, KS, KRED, CLF, BGC

[Org. Biomol. Chem. 20190228135130, 2019, 9−2331]
Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids
(Michigami, Kenichi; Murakami, Hiroki; Nakamura, Takeru; Hayama, Noboru; Takemoto, Yoshiji)
Tag: B, Cat, as, MA, TU

[Chem. Sci. 2019022814001, 2019, 9−2578]
Achieving efficient and robust catalytic reforming on dual-sites of Cu species
(Ma, Kui; Tian, Ye; Zhao, Zhi-Jian; Cheng, Qingpeng; Ding, Tong; Zhang, Jing; Zheng, Lirong; Jiang, Zheng; Abe, Takayuki; Tsubaki, Noritatsu; Gong, Jinlong; Li, Xingang)
Tag: Cat, H, FC, SR, DME, CH3OH, CH3OCH3, HE, ED, C

[Phys. Chem. Chem. Phys. 20190228140238, 2019, 9−5158]
A new ab initio modeling scheme for the ion self-diffusion coefficient applied to the ε-Cu3Sn phase of the Cu–Sn alloy
(Ichibha, Tom; Prayogo, Genki; Hongo, Kenta; Maezono, Ryo)

[Phys. Chem. Chem. Phys. 20190228140245, 2019, 9−5148]
The atomic-scale structure of LaCrO3–NaTaO3 solid solution photocatalysts with enhanced electron population
(Sudrajat, Hanggara; Zhou, Yizhong; Sasaki, Takuro; Ichikuni, Nobuyuki; Onishi, Hiroshi)
Tag: EXAFS, SS, Na, ABS, VL, TM, e-

[Phys. Chem. Chem. Phys. 20190228140327, 2019, 9−5117]
Tailoring widely used ammonia synthesis catalysts for H and N poisoning resistance
(Ghuman, Kulbir Kaur; Tozaki, Kota; Sadakiyo, Masaaki; Kitano, Sho; Oyabe, Takashi; Yamauchi, Miho)
Tag: H, N, NH3, C

[Phys. Chem. Chem. Phys. 20190228140346, 2019, 9−5097]
Ionic transport in highly concentrated lithium bis(fluorosulfonyl)amide electrolytes with keto ester solvents: structural implications for ion hopping conduction in liquid electrolytes
(Kondou, Shinji; Thomas, Morgan L.; Mandai, Toshihiko; Ueno, Kazuhide; Dokko, Kaoru; Watanabe, Masayoshi)
Tag: MAA, Li, Me

[Phys. Chem. Chem. Phys. 20190228140454, 2019, 9−5022]
Perturbative triples correction to domain-based local pair natural orbital variants of Mukherjee{'}s state specific coupled cluster method
(Lang, Jakub; Brabec, JiÅ?Ã; Saitow, Masaaki; Pittner, JiÅ?Ã; Neese, Frank; Demel, OndÅej)
Tag: CC, MR, MRCC, TME, PNO, LPNO, NO

[Soft Matter 20190228141232, 2019, 9−1953]
Shearing-induced contact pattern formation in hydrogels sliding in polymer solution
(Yashima, Shintaro; Hirayama, Satoshi; Kurokawa, Takayuki; Salez, Thomas; Takefuji, Haruna; Hong, Wei; Gong, Jian Ping)

[Soft Matter 20190228141250, 2019, 9−1927]
Flow of wormlike micellar solutions around microfluidic cylinders with high aspect ratio and low blockage ratio
(Haward, Simon J.; Kitajima, Naoyuki; Toda-Peters, Kazumi; Takahashi, Tsutomu; Shen, Amy Q.)
Tag: AR, TD, Mx, Re, TR, as

[Thin Solid Films 20190228141345, 2019, −58]
Thin film deposition method for ZnO nanosheets using low-temperature microwave-excited atmospheric pressure plasma jet
(Shahiduzzaman, Md.; Yamada, Ryosuke; Chikamatsu, Tatsuki; Ono, Tsunehisa; Tanaka, Yasunori; Uesugi, Yoshihiko; Karakawa, Makoto; Kuwabara, Takayuki; Takahashi, Kohshin; Ishijima, Tatsuo; Taima, Tetsuya)
Tag: ZA, NS, acac, SSM, APPJ, ZnO, Zn, PV, Si, OPV, OVD, AP, O, TFT, ECL, e-, TF

[Thin Solid Films 20190228141353, 2019, −103]
Improvement in the passivation quality of catalytic-chemical-vapor-deposited silicon nitride films on crystalline Si at room temperature
(Miyaura, Jun'ichiro; Ohdaira, Keisuke)
Tag: c-Si, Cat, Si, CVD, CCVD

[Thin Solid Films 20190228141434, 2019, −7]
Sol-gel processed niobium oxide thin-film for a scaffold layer in perovskite solar cells
(Inami, Eiichi; Ishigaki, Takamasa; Ogata, Hironori)
Tag: PSC, Ti, PL, XR, EM, Nb, MAPI, ABS, OA, XRD, e-, TF, P, SEM

[Polyhedron 20190228142230, 2019, −111]
Stereoselective formation and spectroscopic studies of [Cr(edda or eddp)(NN)]-type complexes (edda = ethylenediamine-N,N′-diacetate; eddp = ethylenediamine-N,N′-dipropionate)
(Yano, Yumie; Nakayama, Ryoko; Yonemura, Toshiaki)
Tag: ClO4, H, N, O, SS, O, Cr, ABS, HB, o-phen, phen, HB

[J. Alloys Compd. 20190228142942, 2019, −1284]
Ultrafine spherulite Mg alloy with high yield strength
(Matsushita, Masafumi; Masuda, Kohtaro; Waki, Ryohei; Ohfuji, Hiroaki; Yamasaki, Michiaki; Kawamura, Yoshihito; Higo, Yuji)
Tag: HEX, Hx, hcp, LPSO, LPS, fcc

[Acta Biomater. 2019022815022, 2019, −187]
Micropatterning of a 2-methacryloyloxyethyl phosphorylcholine polymer surface by hydrogenated amorphous carbon thin films for endothelialization and antithrombogenicity
(Bito, Kenta; Hasebe, Terumitsu; Maegawa, Shunto; Kitagawa, Tomoya; Matsumoto, Tomohiro; Suzuki, Tetsuya; Hotta, Atsushi)
Tag: MPC, EC, C, HUVEC, HAC, AC, DES, TF

[Acta Biomater. 20190228150323, 2019, −118]
Intervertebral disc regeneration with an adipose mesenchymal stem cell-derived tissue-engineered construct in a rat nucleotomy model
(Ishiguro, Hiroyuki; Kaito, Takashi; Yarimitsu, Seido; Hashimoto, Kunihiko; Okada, Rintaro; Kushioka, Junichi; Chijimatsu, Ryota; Takenaka, Shota; Makino, Takahiro; Sakai, Yusuke; Moriguchi, Yu; Otsuru, Satoru; Hart, David A.; Fujie, Hiromichi; Nakamura, Norimasa; Yoshikawa, Hideki)
Tag: MSC, IVD