3007-95-2Relevant articles and documents
KPF6-Mediated Esterification and Amidation of Carboxylic Acids
Sonam, None,Shinde, Vikki N.,Kumar, Anil
, p. 2651 - 2661 (2022/02/07)
A novel KPF6-promoted green method has been developed for the synthesis of esters and amides. A wide range of carboxylic acids and alcohols or amines worked well under the developed reaction conditions, thus providing good to excellent (61-98%) yields of
Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
, p. 68 - 74 (2021/11/16)
Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
Synthesis of naphthalenecarboxylic and naphthalenedicarboxylic acids from naphthalene, carbon tetrachloride, and alcohols in the presence of iron catalysts
Baiguzina,Erokhina,Khusnutdinov
, p. 389 - 395 (2017/05/01)
Alkyl naphthalenecarboxylates and dialkyl naphthalenedicarboxylates have been synthesized by reactions of naphthalene and its derivatives with alcohols and carbon tetrachloride in the presence of iron catalysts.
Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters
Wang, Lin,Neumann, Helfried,Spannenberg, Anke,Beller, Matthias
supporting information, p. 7469 - 7472 (2017/07/12)
An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.
Synthetic method of an ester compound
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Paragraph 0081; 0082; 0083, (2017/02/02)
The invention discloses a synthetic method of an ester compound and belongs to the technical field of organic synthesis. The synthetic method includes the steps of: dissolving an aldehyde compound (1) and a halogenated hydrocarbon compound (2) in a solvent, adding an oxidant and a catalyst, and performing a reaction at 60-100 DEG C to obtain the target product ester compound (3). A reaction equation of the synthetic method is represented as follows. The method, compared with the prior art, has the following advantages: 1) the raw materials are easy to obtain and are low in cost; 2) the reaction conditions are mild, operations are simple, and reaction time is short; and 3) a substrate has wide available range and can be used for synthesis of various ester compounds.
Expedient carbonylation of aryl halides in aqueous or neat condition
Ang, Wei Jie,Lo, Lee-Chiang,Lam, Yulin
, p. 8545 - 8558 (2014/12/11)
An expedient and versatile, microwave-assisted procedure for the carbonylation of aryl halides with boronic acids, alcohols or amines in water or under neat conditions has been developed. The reaction is catalyzed by fluorous, oxime-based palladacycle 1 that shows an excellent recyclable property and low levels of Pd leaching. To demonstrate the usefulness of the protocol, we applied it to the preparation of compounds of pharmaceutical interest, including a precursor of the reverse transcriptase inhibitor, niacin, benzocaine and butamben.
One-pot transformation of carboxylic acids into nitriles
Miyagi, Kotaro,Moriyama, Katsuhiko,Togo, Hideo
, p. 5886 - 5892 (2013/09/23)
A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. Copyright
Ligand free palladium catalyzed decarboxylative cross-coupling of aryl halides with oxalate monoester salts
Li, Yan,Chen, Huan-Huan,Wang, Chu-Fei,Xu, Xiao-Lan,Feng, Yi-Si
, p. 5796 - 5799 (2012/10/29)
Ligand free Pd-catalyzed decarboxylative cross-coupling of potassium oxalate monoester and derivatives with aryl iodides and bromides is described. Functionalized aromatic esters can be efficiently synthesized via this method with only 1.0 mol % Pd(OAc)2 catalyst without any phosphine ligand. This method illustrates an inexpensive and operationally simple method for the preparation of aromatic esters and acids, which is especially beneficial for a large scale synthesis.
Efficient carbonylation of aryl and heteroaryl bromides under atmospheric pressure of CO
Yang, Weizhun,Han, Wei,Zhang, Weidong,Shan, Lei,Sun, Jiansong
supporting information; experimental part, p. 2253 - 2255 (2011/10/19)
In the presence of Et and n-BuOH, efficient alkoxycarbonylation of (hetero)aromatic bromides was achieved under atmospheric pressure of carbon monoxide with in situ generated palladium/rac-BINAP as catalyst. Georg Thieme Verlag Stuttgart - New York.
Palladium-catalyzed aerobic oxidative carbonylation of arylboronate esters under mild conditions
Liu, Qiang,Li, Gang,He, Jun,Liu, Jing,Li, Peng,Lei, Aiwen
supporting information; experimental part, p. 3371 - 3374 (2010/07/06)
(Figure Presented) "CO"n Air: The title reaction was carried out using [PdCl2(PPh3)2 ] as the catalyst precursor under very mild conditions (balloon pressure of CO and air, at 40- 50°C), and produced a wide range of aryl carboxyl esters 2 in good to excellent yields. Remarkable selectivity between oxidative carbonylation and homocoupling of arylboronate esters l was also achieved.