- Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides
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A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.
- Rajendra, Merla Arjuna,Sunil,Sajith, Ayyiliath Meleveetil,Joy, Muthipeedika Nibin,Bakulev, Vasiliy A.,Haridas, Karickal Raman
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supporting information
p. 1629 - 1633
(2020/09/15)
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- Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides
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A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.
- Arisawa, Mieko,Tanii, Saori,Tazawa, Takeru,Yamaguchi, Masahiko
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supporting information
p. 11390 - 11393
(2016/09/23)
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- Palladium-Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br
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The CF3 group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well-established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl-substituted (hetero)arenes by palladium-catalyzed C-H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio- and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased.
- Natte, Kishore,Jagadeesh, Rajenahally V.,He, Lin,Rabeah, Jabor,Chen, Jianbin,Taeschler, Christoph,Ellinger, Stefan,Zaragoza, Florencio,Neumann, Helfried,Brückner, Angelika,Beller, Matthias
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supporting information
p. 2782 - 2786
(2016/02/27)
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- Silver-Catalyzed C-H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent
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Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl C-H trifluoromethylation, but the generation of CF3· from TFA may prove useful in other contexts and could potentially be extended to other trifluoromethylation reactions. (Chemical Equation Presented).
- Shi, Guangfa,Shao, Changdong,Pan, Shulei,Yu, Jingxun,Zhang, Yanghui
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supporting information
p. 38 - 41
(2015/07/28)
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- Synthesis of 3-trifluoromethyl-4-halobenzonitriles
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The practical synthetic method for a series of substantially novel fluorine-containing polyfunctional aromatic compounds, 3-trifluoromethyl-4-halobenzonitriles [halo = Cl, Br, and F], was established by using copper-cyano complexes as effective Sandmeyer cyanating reagents.
- Yonezawa, Noriyuki,Hino, Tetsuo,Namie, Tsutomu,Katakai, Ryoichi
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p. 1575 - 1578
(2007/10/03)
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