160001-85-4Relevant articles and documents
Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts
Zhang, Cheng-Pan,Cai, Ji,Zhou, Chang-Bing,Wang, Xiao-Ping,Zheng, Xing,Gu, Yu-Cheng,Xiao, Ji-Chang
, p. 9516 - 9518 (2011)
The ligand-free trifluoromethylation of arylboronic acids with a [Ph 2SCF3]+[OTf]-/Cu(0) system has been carefully investigated. Aryl-, alkenyl- and heteroarylboronic acids with a variety of functional groups were suitable substrates for this reaction. It is suggested that a CuCF3 species is formed under the reaction conditions.
DBU-Promoted Trifluoromethylation of Aryl Iodides with Difluoromethyltriphenylphosphonium Bromide
Wei, Yun,Yu, Liuying,Lin, Jinhong,Zheng, Xing,Xiao, Jichang
, p. 481 - 484 (2016)
DBU-promoted trifluoromethylation of aryl iodides with difluoromethyltriphenylphosphonium bromide (DFPB) in the presence of copper source is described. In this transformation, DBU not only acts as base to deprotonate the difluoromethyl group in DFPB to generate difluoromethylene phosphonium ylide Ph3P+CF2-, but also converts the difluorocarbene generated from ylide Ph3P+CF2- into trifluoromethyl anion, finally resulting in the trifluoromethylation of aryl iodides. The reactions proceeded smoothly to afford expected products in moderate to good yields.
Ligand-dependent formation of ion-pair CuI/CuIII trifluoromethyl complexes containing bisphosphines
Zhang, Song-Lin,Bie, Wen-Feng
, p. 17588 - 17592 (2016)
We report novel ion-pair bisphosphine CuI/CuIII trifluoromethyl complexes [(P2)2CuI]+[CuIII(CF3)4]- (P2 = DPPE, BINAP or Xantphos) fea
Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines
Dorsheimer, Julia R.,Ashley, Melissa A.,Rovis, Tomislav
supporting information, p. 19294 - 19299 (2021/11/23)
We report a method to activate α-3° amines for deaminative arylation via condensation with an electron-rich aldehyde and merge this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers, a common motif in pharmaceuticals and natural products. The reaction is accelerated by added ammonium salts. Evidence is provided in support of two roles for the additive: inhibition of nickel black formation and acceleration of the overall reaction rate. We demonstrate a robust scope of amine and haloarene coupling partners and show an expedited synthesis of ALK2 inhibitors.
Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes
Bartfield, Noah M.,Frederich, James H.,Law, James A.
supporting information, p. 14360 - 14364 (2021/05/27)
Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp2Ti(μ-Cl)(μ-CH2)AlMe2 (Tebbe's reagent) and unactivated alkenes. Protonolysis of the resulting titanacyclobutanes in situ effects hydromethylation in a chemo-, regio-, and site-selective manner. The broad utility of this method is demonstrated across a series of mono- and di-substituted alkenes containing pendant alcohols, ethers, amides, carbamates, and basic amines.