Viewed: 08:37:21 in April 9, 2020

Synthesis of Allylboranes via Cu(I)-Catalyzed B–H Insertion of Vinyldiazoacetates into Phosphine–Borane Adducts (Drikermann, Denis; Mößel, Robert S.; Al-Jammal, Walid K.; Vilotijevic, Ivan)
Org. Lett. 2020, 22 (3), 1091−1095.

Keywords: Cu; borane tributylphosphine complex; BOX; BARF; 読みたい論文シリーズ; 有機化学; ブログ

銅触媒下でのジアゾアリル化合物とボランホスフィン錯体の反応によるアリルボランホスフィン錯体合成とその利用に関する論文のようです。

基質合成の容易さなどの事情があるのか、アルコキシカルボニル基のついたジアゾアリル化合物、言い換えれば&alpha位にアリル基の結合したアゾ酢酸エステルに限定された反応です。それ以外のタイプのジアゾ化合物の反応例が報告されているのかこの研究中で行われているのかは、本文を読まないとわからないので、読みたい論文に追加しました。

この論文の反応がそうであるように、ジアゾ化合物といえば挿入反応。昔よく見かけたのがジアゾメタンとカルボン酸の反応。メチルエステルが生成します。毒々しく危なっかしくで、やりたくない実験の一つでした。他、ヒドロシランの反応で光学活性シランを合成したりとか。遷移金属触媒を使用する反応例もあり、この論文の反応と同じような機構を経て進むと思うのですが、どんな素反応の組み合わせだったのかはすっかり忘れてしまいました。勉強し直しです。

時々忘れるNaBArFの構造。

　

 

☆ジアゾ化合物とアゾ化合物

ジアゾ化合物は、R–N₂で表される有機化合物。
アゾ化合物は、R–N=N–R'で表される有機化合物。

 

pic.twitter.com/MWfEqDob4P

— nanoniele (@nanoniele) February 9, 2020

 

　

 

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[J. Mater. Chem. A 2020, 8, 2171−2206]
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[J. Mater. Chem. A 2020, 8, 2349−2355]
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[J. Mater. Chem. A 2020, 8, 2490−2497]
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[J. Mater. Chem. A 2020, 8, 2581−2590]
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[J. Mater. Chem. A 2020, 8, 2760−2768]
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[Dalton Trans. 2020, 49, 1384−1387]
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[Dalton Trans. 2020, 49, 1416−1423]
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[Dalton Trans. 2020, 49, 1485−1491]
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[ACS Catal. 2020, 10, 1454−1459]
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[ACS Catal. 2020, 10, 921−932]
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Tag: HTS, Sn, HT, OCM, C2H6, ML, C, CH4

[ACS Catal. 2020, 10, 1010−1023]
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[ACS Appl. Mater. Interfaces 2020, 12, 6144−6150]
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Tag: TP, BT, BTDA, D-A, PL, Sn, TPH, ABS, FET, VL, cbz, OFET, curr.

[ACS Appl. Mater. Interfaces 2020, 12, 6496−6502]
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Tag: MI, LBL, evapd., TP, PSC, PV, Si, Sn, TPH, I, HTM, VPP, HTL, PCE, polymn., EL, DOF, P, TSC

[ACS Appl. Mater. Interfaces 2020, 12, 6641−6650]
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[ACS Appl. Mater. Interfaces 2020, 12, 6662−6676]
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[ChemPhysChem 2020, 21, 175−180]
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[Chem. Asian. J. 2020, 15, 294−300]
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[Chem. Sci. 2020, 11, 1205−1209]
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[Org. Biomol. Chem. 2020, 18, 851−855]
Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst
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Tag: 2-Np, 2-Naph, TCA, Naph, Nap, Np, C

[Org. Biomol. Chem. 2020, 18, 999−1011]
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[Org. Biomol. Chem. 2020, 18, 999−1011]
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Tag: Sn

[J. Mater. Chem. C 2020, 8, 1736−1745]
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[J. Mater. Chem. C 2020, 8, 1746−1754]
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[J. Mater. Chem. C 2020, 8, 1811−1818]
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[J. Phys. Chem. C 2020, 124, 2879−2885]
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Tag: SE, pc, MR, EC, Sn, FC, O, La, 57-13-6, MDS, YSZ, OV, Ovac, LSO, MD, SOFC, NMR, Ea

[J. Phys. Chem. C 2020, 124, 2953−2960]
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Tag: n.r., NR, C, EM, FT, TWC, NP, morphol., morph., TEM, e-, C, IR, DFT, Cat

[J. Phys. Chem. C 2020, 124, 2968−2977]
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Tag: VdW, EELS, NO, STM, expt., EEL, e-, M

[J. Phys. Chem. C 2020, 124, 3196−3203]
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Tag: PEC, APXPS, fac, PE, ES, Fe, EC, Sn, XPS, O, PEC, PS, EEI, thermodn., HV, UHV, e-

[J. Phys. Chem. C 2020, 124, 3242−3249]
Whispering Gallery Mode Lasing from CH₃NH₃PbBr₃/PEO Composites Grown in a Microcapillary
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Tag: TRPL, QED, PEO, Et, TR, PL, Sn, am, WGM, EO, morphol., morph., Me, C2H4, P, PE

[J. Phys. Chem. C 2020, 124, 3250−3259]
Role of Depolarization Factors in the Evolution of a Dipolar Plasmonic Spectral Line in the Far- and Near-Field Regimes
(Januar, Mochamad; Liu, Bei; Cheng, Jui-Ching; Hatanaka, Koji; Misawa, Hiroaki; Hsiao, Hui-Hsin; Liu, Kou-Chen)
Tag: SPR, Sn, SP, LSPR, LSP

[J. Phys. Chem. C 2020, 124, 3277−3286]
Effect of the Tris(trimethylsilyl)silyl Group on the Fluorescence and Triplet Yields of Oligothiophenes
(Hirata, Shuzo; Nishio, Masaki; Uchida, Hikaru; Usuki, Tsukasa; Nakae, Toyotaka; Miyachi, Mariko; Yamanoi, Yoshinori; Nishihara, Hiroshi)
Tag: TTMS, OMO, ISC, TP, Et, FL, Sn, TPH, OTH, TA, MO, ABS, TMS, FLY, RTF, Me, TTMSS, HOMO

[J. Phys. Chem. C 2020, 124, 3314−3321]
Energy-Efficient Stacks—Covellite (CuS) on Polyethylene Terephthalate Film: A Sustainable Solution to Heat Management
(Rath, Ashutosh; Chua, Sing Teng; Okano, Shun; Pennycook, Stephen J.; Okano, Ken)
Tag: RF, pht, est., PETE, Et, PET, Sn, HT, oxidn., NIR, curr., C2H4, TF, IR, PE

[J. Phys. Chem. C 2020, 124, 3322−3331]
Understanding Single-Molecule Parallel Circuits on the Basis of Frontier Orbital Theory
(Okazawa, Kazuki; Tsuji, Yuta; Yoshizawa, Kazunari)
Tag: Sn, NH2, NEQ, curr., e-, CSL

[J. Phys. Chem. B 2020, 124, 788−797]
Light-Induced Nanosecond Relaxation Dynamics of Rhenium-Labeled Pseudomonas aeruginosa Azurins
(Pospíšil, Petr; Sýkora, Jan; Takematsu, Kana; Hof, Martin; Gray, Harry B.; Vlček, Antonín)
Tag: ET, Et, AA, TR, em, St, Sn, His, H, PSS, o-phen, phen, Me, SC, e-

[J. Phys. Chem. B 2020, 124, 848−860]
Complementary Effect of Intra- and Intermolecular Hydrogen Bonds on Electron Transfer in β-Hydroxy-Anthraquinone Derivatives
(Nakayama, Tatsushi; Okumura, Noriko; Uno, Bunji)
Tag: ACN, AN, ANT, MeCN, ET, C, H, EC, Sn, O, ANQ, AQN, AQ, ipso, e-, HB, HB, OEt

[J. Phys. Chem. B 2020, 124, 881−889]
Atomistic Mechanism of Anisotropic Heat Conduction in the Liquid Crystal 4-Heptyl-4′-cyanobiphenyl: All-Atom Molecular Dynamics
(Sasaki, Ryoma; Takahashi, Yuki; Hayashi, Yoshihiro; Kawauchi, Susumu)
Tag: TC, Hep, det., Hept, MI, LC, LJ, CN, Sn, MDS, NLC, lemonene, MD, decompn., LC, expt., FF, Ph, PTT, AAMD

[J. Phys. Chem. A 2020, 124, 824−835]
Thermal Decomposition of Benzyl Radicals: Kinetics and Spectroscopy in a Shock Tube
(Matsugi, Akira)
Tag: det., Fe, est., IS, C, TR, R, Sn, Bn, HC, TA, ABS, arene, decompn., BBCEAS

[J. Phys. Chem. A 2020, 124, 1053−1061]
Two-Dimensional Electronic Spectroscopy Using Rotating Optical Flats
(Tapping, Patrick C.; Song, Yin; Kobayashi, Yoichi; Scholes, Gregory D.; Kee, Tak W.)
Tag: 2DES, Sn, expt., e-

[Cryst. Growth Des. 2020, 20, 590−599]
Crystal Structure Analysis and Pharmaceutical Properties of Amide Salts Consisting of Paracetamol/Sulfonic Acids as Solid Forms Prepared by Grinding
(Suzuki, Naoto; Kanazawa, Takanori; Takatori, Kazuhiko; Suzuki, Toyofumi; Fukami, Toshiro)
Tag: pptn., C, Sn, 57-13-6, PhMe, TosOH, TSA, NpH, APRA, AP, pAP, C2H6, PhOH, TolH, SC

[Cryst. Growth Des. 2020, 20, 874−883]
Inverse Temperature Crystallization of Formamidinium Tin Iodide: Indirect Transition State and Restriction of Cation Motion
(Sekimoto, Takeyuki; Suzuka, Michio; Yokoyama, Tomoyasu; Miyamoto, Yoshiko; Uchida, Ryusuke; Hiraoka, Maki; Kawano, Kenji; Sekiguchi, Takashi; Kaneko, Yukihiro)
Tag: AN, MR, TS, PL, SS, Sn, VL, MRS, GVL, NBG, ITC, SC, NMR

[Cryst. Growth Des. 2020, 20, 906−915]
Selective Synthesis of a Salt and a Cocrystal of the Ethionamide–Salicylic Acid System
(Bernasconi, Davide; Bordignon, Simone; Rossi, Federica; Priola, Emanuele; Nervi, Carlo; Gobetto, Roberto; Voinovich, Dario; Hasa, Dritan; Duong, Nghia Tuan; Nishiyama, Yusuke; Chierotti, Michele R.)
Tag: HS, H, SS, Sn, XR, SCXRD, EthA, Sal, thermodn., expt., XRD, SC, DFT

[Cryst. Growth Des. 2020, 20, 1047−1057]
Stereocomplex and Individual Crystallizability of Random Copolymers Based on Chiral α-Monosubstituted 2-Hydroxyalkanoic Acids
(Tsuji, Hideto; Osanai, Katsuya; Arakawa, Yuki)
Tag: det., PLLA, L-Lac, Et, RCP, Sn, GA, Me, M

[Cryst. Growth Des. 2020, 20, 1097−1102]
Gear Alignments Due to Hydrogen-Bonded Networks in a Crystal Structure of Resorcyltriptycene Hydrate and Its Transformation to a Nongearing Anhydrate Crystal by Heating
(Tanaka, Noriyuki; Inagaki, Yusuke; Yamaguchi, Kentaro; Setaka, Wataru)
Tag: Trp, H, Sn, CH3CH2OH, PhMe, CH3OH, TPC, Ph, TolH, SC, HB, EtOH

[Cryst. Growth Des. 2020, 20, 1276−1284]
Density and Dimensional Control of π-Electrons in Electrostatically Binding Naphthalenediimide Salts
(Kawasaki, Ayumi; Takeda, Takashi; Hoshino, Norihisa; Matsuda, Wakana; Seki, Shu; Akutagawa, Tomoyuki)
Tag: det., OMO, UMO, MI, LUMO, FP, FP-TRMC, dil., ES, H, TR, IX, TRMC, Sn, am, MO, PhH, BZ, UC, NpH, TI, deid., e-, SC, M, HB, HB, Alk

[Biochemistry 2020, 59, 351−363]
Precise Probing of Residue Roles by NRPS Code Swapping: Mutation, Enzymatic Characterization, Modeling, and Substrate Promiscuity of Aryl Acid Adenylation Domains
(Ishikawa, Fumihiro; Nohara, Maya; Nakamura, Shinya; Nakanishi, Isao; Tanabe, Genzoh)
Tag: Fe, NRPS, NRP, AA, Sn, DHBA, DHBA, Sal, BZA, BzOH, Ar

[Biochemistry 2020, 59, 400−406]
Thermus thermophilus DNA Ligase Connects Two Fragments Having Exceptionally Short Complementary Termini at High Temperatures
(Wang, Jing; Zhu, Jianming; Wang, Chenru; Zhou, Guangqing; Yu, Xin; Fan, Huijun; An, Ran; Komiyama, Makoto; Liang, Xingguo)
Tag: Sn, HRM, curr., HRM

[Biochemistry 2020, 59, 520−529]
Allosteric Communication with the Retinal Chromophore upon Ion Binding in a Light-Driven Sodium Ion-Pumping Rhodopsin
(Otomo, Akihiro; Mizuno, Misao; Inoue, Keiichi; Kandori, Hideki; Mizutani, Yasuhisa)
Tag: RR, Rh, Rb, Ra, RR, H, K, Sn, Na, 57-13-6, ABS, RRS, SB, KR2, HB

[Biochemistry 2020, 59, 563−581]
Interaction Energetics and Druggability of the Protein–Protein Interaction between Kelch-like ECH-Associated Protein 1 (KEAP1) and Nuclear Factor Erythroid 2 Like 2 (Nrf2)
(Zhong, Mengqi; Lynch, Andrew; Muellers, Samantha N.; Jehle, Stefan; Luo, Lingqi; Hall, David R.; Iwase, Reina; Carolan, James P.; Egbert, Megan; Wakefield, Amanda; Streu, Kristina; Harvey, Christine M.; Ortet, Paula C.; Kozakov, Dima; Vajda, Sandor; Allen, Karen N.; Whitty, Adrian)
Tag: BE, Ala, A, Sn, BDE, SMI

[ACS Sustainable Chem. Eng. 2020, 8, 1730−1740]
Life Cycle Greenhouse Gas Emissions of Long and Pure Carbon Nanotubes Synthesized via On-Substrate and Fluidized-Bed Chemical Vapor Deposition
(Teah, Heng Yi; Sato, Toshihiro; Namiki, Katsuya; Asaka, Mayu; Feng, Kaisheng; Noda, Suguru)
Tag: NT, Fe, C, em, Sn, CF, GHG, CVD, CNT, expt., C

[ACS Sustainable Chem. Eng. 2020, 8, 1908−1915]
Synthesis and Electrochemical Reaction of a Pitch Carbon-Coated Zinc Vanadium Oxide Anode with Excellent Electrochemical Performance for Rechargeable Lithium Batteries
(Jo, Jae Hyeon; Choi, Ji Ung; Kim, Hee Jae; Yashiro, Hitoshi; Myung, Seung-Taek)
Tag: TOF-SIMS, IS, TOF, ET, C, EC, Li, Sn, XR, ret, ABS, SIMS, XAS, XRD, e-, MS