477191-79-0Relevant articles and documents
FLUORESCENT DYE FILMS FOR DETECTING NOx-BASED EXPLOSIVES IN THE AIR, IN SOLUTIONS, AND FROM WIPE SAMPLES
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, (2019/01/10)
A detection reagent for an analyte comprising a NOx-based group, wherein the detection reagent comprises an aryl amine and a structural formula of the aryl amine is selected from structural formulas 1, 2 or 3: wherein R1 is selected from COsub
Transition-metal-free hydrogenation of aryl halides: From alcohol to aldehyde
Zheng, Hong-Xing,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
, p. 5114 - 5117 (2017/11/07)
A transition-metal-and catalyst-free hydrogenation of aryl halides, promoted by bases with either aldehydes or alcohols, is described. One equivalent of benzaldehyde affords an equal yield as that of 0.5 equiv of benzyl alcohol. The kinetic study reveals that the initial rate of PhCHO is much faster than that of BnOH, in the ratio of nearly 4:1. The radical trapping experiments indicate the radical nature of this reaction. Based on the kinetic study, trapping and KIE experiments, and control experiments, a tentative mechanism is proposed. As a consequence, a wide range of (hetero)aryl iodides and bromides were efficiently reduced to their corresponding (hetero)arenes. Thus, for the first time, aldehydes are directly used as hydrogen source instead of other well-established alcohol-hydrogen sources.
Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
Tezuka, Noriyuki,Shimojo, Kohei,Hirano, Keiichi,Komagawa, Shinsuke,Yoshida, Kengo,Wang, Chao,Miyamoto, Kazunori,Saito, Tatsuo,Takita, Ryo,Uchiyama, Masanobu
supporting information, p. 9166 - 9171 (2016/08/05)
Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
Organoaluminum-Mediated Direct Cross-Coupling Reactions
Minami, Hiroki,Saito, Tatsuo,Wang, Chao,Uchiyama, Masanobu
supporting information, p. 4665 - 4668 (2015/04/14)
We present a direct cross-coupling reaction between arylaluminum compounds (ArAlMe2·LiCl) and organic halides RX (R=aryl, alkenyl, alkynyl; X=I, Br, and Cl) without any external catalyst. The reaction takes place smoothly, simply upon heating, thereby enabling the efficient and chemo-/stereoselective formation of biaryl, alkene, and alkyne coupling products with broad functional group compatibility.
High-yielding, versatile, and practical [Rh(III)Cp*]-catalyzed ortho bromination and iodination of arenes
Schroeder, Nils,Wencel-Delord, Joanna,Glorius, Frank
, p. 8298 - 8301 (2012/06/29)
We report a uniquely high-yielding, general, and practical ortho bromination and iodination reaction of different classes of aromatic compounds. This reaction occurs by Rh(III)-catalyzed C-H bond activation methodology and is therefore the first example of the application of this cationic catalyst for C-Br and C-I bond formation.
Development of highly chemoselective bulky zincate complex, tBu 4ZnLi2: Design, structure, and practical applications in small-/macromolecular synthesis
Furayama, Taniyuki,Yonehara, Mitsuhiro,Arimoto, Sho,Kobayashi, Minoru,Matsumoto, Yotaro,Uchiyama, Masanobu
supporting information; experimental part, p. 10348 - 10356 (2009/10/10)
We present full details of the unique reactivities of the newly developed dianion-type bulky zincate, dilithium tetra-ferf-butylzincate (tBu 4ZnLi2). With this reagent, halogen-zinc exchange reaction of variously functionalized haloaromatics and anionic polymerization of N-isopropylacrylamide (NIPAm)/styrene with excellent chemoselectivity were realized. Halogen-zinc exchange reaction followed by electrophilic trapping with propargyl bromide provided a convenient route to functionalized phenylallenes, particularly those with electrophilic functional groups (such as cyano, amide and halogens). Spectral and computational studies of the structure in the gas and liquid phases indicated extraordinary stabilization of this dianion-type zincate by its bulky ligands.
Toward a protecting-group-free halogen-metal exchange reaction: Practical, chemoselective metalation of functionalized aromatic halides using dianion-type zincate,tBu4ZnLi2
Uchiyama, Masanobu,Furuyama, Taniyuki,Kobayashi, Minoru,Matsumoto, Yotaro,Tanaka, Kentaro
, p. 8404 - 8405 (2007/10/03)
A versatile preparation method for aromatic zincate compounds through a halogen-zinc exchange reaction using dilithium tetra-tert-butylzincate (tBu4ZnLi2) has been developed. This reagent permits efficient preparation of highly functionalized aromatic zincates, particularly, those with electrophilic functional groups, such as ester, amide, alcohol, and phenol. Halogen-zinc exchange reactions followed by electrophilic trapping (with allyl bromide or benzaldehyde) proved to be a powerful tool for C-C bond formation on functionalized aromatic rings. The functionalized aromatic zincate intermediate was also found to undergo copper- and palladium-catalyzed C-C bond-forming reactions with good yields and high chemoselectivity. Copyright
