67743-49-1Relevant academic research and scientific papers
Selective Acylation of Aryl- A nd Heteroarylmagnesium Reagents with Esters in Continuous Flow
Heinz, Benjamin,Djukanovic, Dimitrije,Ganiek, Maximilian A.,Martin, Benjamin,Schenkel, Berthold,Knochel, Paul
, p. 493 - 496 (2020/01/31)
A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or Grignard was crucial for the reaction outcome. This was leveraged by the obtention of several bisaryl ketones using 2-hydroxy ester derivatives as substrates.
Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation
Liu, Kui,Tao, Shou-Wei,Qian, Chun,Zhu, Yong-Ming
supporting information, p. 4769 - 4775 (2018/09/06)
A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.
A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
Ramakrishna, Visannagari,Rani, Morla Jhansi,Reddy, Nareddula Dastagiri
, p. 7238 - 7255 (2018/01/01)
The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.
Exploring the Reducing Ability of Organic Dye (Acr+-Mes) for Fluorination and Oxidation of Benzylic C(sp3)-H Bonds under Visible Light Irradiation
Xiang, Ming,Xin, Zhi-Kun,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 3009 - 3012 (2017/06/07)
The excellent oxidizing capability of acridinium-based organic dye (Acr+-Mes) is fully studied in photoredox catalysis. However, its reducing ability is always considered weak for organic transformation. The reducing ability of Acr+-Mes is developed by Selectfluor to achieve effective fluorination and oxidation of benzylic C(sp3)-H bonds under visible light irradiation, which is not available for the direct use of oxidizing ability of excited Acr+-Mes. Mechanistic insights provided strong evidence for the oxidative quenching of Acr+-Mes.
Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates
Jin, Fengli,Han, Wei
supporting information, p. 9133 - 9136 (2015/06/08)
We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows wide scope with regard to both aryl halides and potassium aryl trifluoroborates containing a series of active functional groups.
Reactions of some p-Substituted Triphenylmethyl Chlorides with Alcohols, Alkali-metal Alcoholates, and Tributylamine
Izso, Gyoengyi,Huszthy, Peter,Lempert, Karoly,Fetter, Jozsef,Simig, Gyula,et al.
, p. 769 - 778 (2007/10/02)
The p-methoxylated triphenylmethyl chlorides (4a-c), when heated with alcohols, give mixtures of the corresponding triarylmethanes (5a-c) (via the hydride transfer to the corresponding triarylmethylium cations) and the alkyl (substituted triphenylmethyl) ethers (7a-c) (via polar susbtitution reactions).Part or all of the ether (7c) may be further converted into the substituted triphenylmethanol (6c).In the reaction of the mono-p-methoxylated halides (4a) and (4c) with methanol, the substitution products (7a) and (7c) are formed as the main products, while the main product of the reaction of the di-p-methoxylated halide (4b) with methanol is the substituted triphenylmethane (5b).When the methanol is replaced by 2H4> methanol, no reduction product is formed from the halide (4c).Reaction of halide (4c) with ethanol furnishes exclusively the substituted triphenylmethane (5c).The p-chlorophenyl(diphenyl)methyl chloride (4d) gives, with methanol, mainly or exclusively the ether (7d), and with ethanol, under mild conditions, gives the ether (9d).However, under vigorous conditions, the substituted triphenylmethane (5d) is formed.The reduction of the p-methoxylated triphenylmethyl chloride (4c) by alcohols as well as its conversion into alkyl (p-methoxylated triphenylmethyl) ethers are accompanied, to a certain degree, by exchange of the p-methoxy group of the substrate and the alkoxy group of the alcohol; no similar exchange of the p-chlorine atom of halide (4d) was observed.Explanations for all obsrved diferences are offered.The reactions of the substituted triphenylmethyl chlorides (4b-d) with alkoxides in the corresponding alcohols give the corresponding alkyl (substituted triphenylmethyl) ethers (7b), (7c), (9c), and (9d), respectively, in excellent yields.The reaction of the triarylmethyl chloride (4d) with potassiumt-butoxide in THF in the presence of acetone led, among other products, to the formation of oligomeric material which indicates the operation of single-electron-transfer induced processes.Reaction of the same chloride (4d) with tributylamine in refluxing cumene or t-butylbenzene led to the exclusive formation of a series of products all of which may be derived from the intermediacy of the substituted triphenylmethyl radical (18); the latter, in turn, is thought to arise as a result of dissociative electron transfer from tributylamine to chloride (4d).
