1443-80-7Relevant articles and documents
A mechanistic study on modern palladium catalyst precursors as new gateways to Pd(0) in cationic Heck reactions
Svennebring, Andreas,Sj?berg, Per J.R.,Larhed, Mats,Nilsson, Peter
, p. 1808 - 1812 (2008)
Electrospray ionization mass spectrometry (ESI-MS) was used as a means to directly identify catalytic cationic organopalladium species in ligand-controlled Heck reactions involving electron-rich olefins and different Pd-sources. In these high-temperature Heck arylations, the oxidative addition intermediates were observed as bidentate ligand chelated cationic aryl palladium species, suggesting that the used ligand attaches to the metal center at the very beginning of the catalytic cycle. This was also in agreement with the obtained regioisomeric profile of the isolated products. The investigation supports the standard Pd(0)/Pd(II) Heck mechanism and provides further insight regarding the conceivable composition of fundamental Pd(II) intermediates in an ongoing Heck reaction.
Copper-catalyzed cyanation of aryl iodide with the combined cyanide source of urea and DMSO
Zheng, Kui,Liu, Bin,Chen, Shuyou,Chen, Fan
, p. 5250 - 5252 (2013)
A simple copper-catalyzed cyanation of aryl iodide with the combination of urea and dimethyl sulfoxide as a cyanide source is achieved, providing nitriles in moderate to good yields. This new approach represents an exceedingly practical and safe method for the synthesis of aryl nitriles.
Copper- and silver-mediated cyanation of aryl iodides using ddq as cyanide source
Zheng, Kui,Yu, Peng,Chen, Shuyou,Chen, Fen,Cheng, Jiang
, p. 449 - 452 (2013)
A new copper and silver-mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved, providing nitriles with good yields. This new approach represents a safe method leading to aryl nitriles. A new copper and silver-mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved.
Optimisation and scale-up of microwave assisted cyanation
Pitts, Michael R.,McCormack, Peter,Whittall, John
, p. 4705 - 4708 (2006)
A microwave enhanced palladium catalysed cyanation procedure was optimised for the final step of a production method for citalopram 2. The method was demonstrated on multigram batch scale for the synthesis of escitalopram (S)-2 and then in a stop-flow continuous process for citalopram.
Palladium-catalyzed cyanation of aryl halides using K4[Fe(CN)6] as cyanide source, water as solvent, and microwave heating
Velmathi, Sivan,Leadbeater, Nicholas E.
, p. 4693 - 4694 (2008)
A methodology for the cyanation of aryl iodides and activated aryl bromides is reported using water as the solvent and K4[Fe(CN)6] as the cyanide source. Reactions are complete within 20 min.
Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein
Geng, Haoxing,Liu, Xin,Zhu, Qing
supporting information, (2021/12/20)
An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.
Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions
Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu
, p. 12344 - 12353 (2021/09/02)
A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.
Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds
Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong
, p. 2134 - 2141 (2021/09/29)
A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]
Erratum: Ruthenium-catalyzed C-H hydroxylation in aqueous acid enables selective functionalization of amine derivatives (Journal of the American Chemical Society (2017) 139:28 (9503-9506) DOI: 10.1021/jacs.7b05469)
Mack, James B.C.,Gipson, John D.,Du Bois,Sigman, Matthew S.
supporting information, p. 3016 - 3016 (2021/03/01)
Page 9504. The structure of product 3cc in Table 2 was found to be mis-assigned. We thank Prof. Phil Baran and Dr. Rafael Navratil for bringing this error to our attention. The correct structure contains an additional benzylic alcohol at the C-9 position of the steroid (3cc′, shown below). With the accompanying change in molecular weight, the isolated yield is 29%. Supporting Information. The incorrect structure and yield also appeared on pages S20 and S84 in the SI. Given this, the HRMS entry on page S20 should read as follows: “HRMS (ESI-TOF) m/z calcd for C19H18F3O5S+ (M-O+Na)+ 415.0822, found 415.0857”. The complete corrected SI is provided here.
HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls
Ding, Ling,Liu, Yuxiu,Niu, Kaikai,Shi, Xiaodi,Song, Hongjian,Wang, Qingmin
, (2021/12/13)
The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.
