1018-97-9Relevant articles and documents
Synthesis of Symmetrical Diaryl Ketones by Cobalt-Catalyzed Reaction of Arylzinc Reagents with Ethyl Chloroformate
Rérat, Alice,Michon, Christophe,Agbossou-Niedercorn, Francine,Gosmini, Corinne
, p. 4554 - 4560 (2016)
Symmetrical diaryl ketones were prepared by a cross-coupling reaction between aryl bromides and ethyl chloroformate. This new method, which uses a catalyst composed of CoBr2and a bipyridine ligand along with readily available starting materials, allows for the synthesis of a variety of symmetrical diaryl ketones in moderate to excellent yields (37–99 %) under mild conditions. This reaction, in which ethyl chloroformate acts as a surrogate of carbon monoxide in the presence of cobalt and zinc, represents an interesting alternative to previously known approaches for the synthesis of diarylmethanones.
Palladium imine-pyridine-imine complex immobilized on graphene oxide as a recyclable catalyst for the carbonylative homo-coupling of aryl halides
Niakan, Mahsa,Asadi, Zahra,Khosrozadeh, Fatemeh
, p. 850 - 863 (2021)
A heterogeneous 3-N,N,N-(II) Pd(OAc)2 catalyst was prepared from the reaction of Pd(OAc)2 with Si-Prn-N = C-Py-C = N-Prn-Si immobilized on graphene oxide (GO-Si-Prn-N = C-Py-C = N-Prn-Si-GO). The prepared catalyst was characterized by inductively coupled plasma optical emission spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, Raman spectroscopy, energy dispersive X-ray spectroscopy, X-ray diffraction, UV-vis spectroscopy, BET surface area, scanning electron microscopy, transmission electron microscopy, and thermogravimetric analysis. The catalyst was employed as a heterogeneous catalyst for carbonylative homo-coupling of aryl iodides and bromides under carbon monoxide gas-free condition. Cr(CO)6 was used as the carbon monoxide source and the desired symmetrical diaryl ketones were achieved in good to excellent yields. Moreover, the catalyst was reused up to five consecutive cycles without significant loss of activity.
Simple preparation of aryltributylstannanes and its application to one-pot synthesis of diaryl ketones
Oikawa, Asuka,Kindaichi, Gan,Shimotori, Yasutaka,Okimoto, Mitsuhiro,Hoshi, Masayuki
, p. 1705 - 1711 (2015)
Transfer of aryl group from boron to tin can be achieved by simple treatment of arylboronic acids with tributyltin methoxide at 100 °C for 1 h under neat conditions. The resulting aryltributylstannanes are applicable to one-pot synthesis of diaryl ketones. Thus, Pd-catalyzed cross-coupling reaction with aroyl chlorides is allowed to proceed without isolation step to produce the corresponding diaryl ketones in good to high yields.
Facile Palladium-Catalyzed Carbonylation of Triarylstibines in the Presence of Ammonium Cerium(IV) Nitrate
Cho, Chan Sik,Tanabe, Koichiro,Itoh, Osamu,Uemura, Sakae
, p. 274 - 275 (1995)
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Ultrafast Chemistry: Cobalt Carbonyl-Mediated Synthesis of Diaryl Ketones under Microwave Irradiation
Enquist, Per-Anders,Nilsson, Peter,Larhed, Mats
, p. 4875 - 4878 (2003)
(Equation Presented) By combining the advantages of metal activation, in situ carbon monoxide delivery, and microwave heating, benzophenones were efficiently synthesized in 6-10 s. These ultrafast carbonylation reactions occur under air by flash heating o
Nickel-Catalyzed Molybdenum-Promoted Carbonylative Synthesis of Benzophenones
Peng, Jin-Bao,Wu, Fu-Peng,Li, Da,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
, p. 6788 - 6792 (2018)
A nickel-catalyzed molybdenum-promoted carbonylative coupling reaction for the synthesis of benzophenones from aryl iodides has been developed. Various substituted diaryl ketones were synthesized in moderate to excellent yields under CO-gas-free conditions. A synergetic effect of both nickel and molybdenum has been observed, which is also responsible for the success of this transformation.
Phosphine ligand triggered oxidative decarbonylative homocoupling of aromatic aldehydes: Selectively generating biaryls and diarylketones
Yang, Luo,Zeng, Tieqiang,Shuai, Qi,Guo, Xiangyu,Li, Chao-Jun
, p. 2161 - 2163 (2011)
A novel rhodium-catalyzed oxidative decarbonylative homocoupling of aromatic aldehydes to generate biaryls and diarylketones selectively and efficiently, triggered by the choice of different phosphine ligands.
N-Heterocyclic Carbene-Catalyzed Synthesis of Ynones via C-H Alkynylation of Aldehydes with Alkynyliodonium Salts - Evidence for Alkynyl Transfer via Direct Substitution at Acetylenic Carbon
Rajkiewicz, Adam A.,Wojciechowska, Natalia,Kalek, Marcin
, p. 831 - 841 (2020/01/02)
Alkynylation of aldehydes with alkynyl(aryl)iodonium salts catalyzed by an N-heterocyclic carbene (NHC) has been developed. The application of the organocatalyst and the hypervalent iodine group transfer reagent allowed for metal-free C-H functionalization and C-C bond formation. The reaction proceeds under mild conditions, at -40 °C and in the presence of an amine base, providing access to an array of heteroaryl-propargyl ketones containing various substituents in good to excellent yields. The mechanism of the reaction was investigated by means of both experiments and density functional theory calculations. 13C-labeling and computations determined that the key alkynyl transfer step occurs via an unusual direct substitution at an acetylenic carbon, wherein an iodine-based leaving group is exchanged by a Breslow intermediate nucleophile. Moreover, kinetic studies revealed that the turnover-limiting step of the catalytic cycle is the generation of the Breslow intermediate, whereas the subsequent C-C bond formation is a fast process. These results are fully reproduced and rationalized by the calculated full free energy profile of the reaction, showing that the largest energy span is located between the protonated form of NHC catalyst and the transition state for the carbene attack on the aldehyde substrate.
Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF3Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols
Chen, Zhi-Min,Ding, Tong-Mei,Ke, Hua,Luo, Hui-Yun,Zhu, Deng
supporting information, p. 7699 - 7703 (2020/10/09)
A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trifluoromethyl sulfoxides was developed. Various allylic and allenic trifluoromethyl sulfoxides were obtained with moderate to excellent yields. Meanwhile, a Lewis acid mediated trifluoromethylthiolation/1,2-rearrangement to synthesize β-SCF3 carbonyl compounds was also accomplished. These two tandem reactions feature with mild reaction conditions and metal-free. During these two reactions, the chemoselectivity of electrophilic trifluoromethylthiolation was revealed.