- Iron-catalysed 1,2-aryl migration of tertiary azides
-
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
- Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
-
p. 11685 - 11688
(2020/10/19)
-
- Oxidative heck arylation for the stereoselective synthesis of tetrasubstituted olefins using nitroxides as oxidants
-
One, two, and three! Nitroxides and dioxygen serve as oxidants in highly stereoselective oxidative Pd-catalyzed Heck arylations in which aryl boronic acids are used to synthesize triarylalkyl-substituted olefins. The reactions occur under very mild conditions at room temperature. As an example, the threefold sequential arylation of methyl acrylate is the crucial step in the stereoselective synthesis of Z-Tamoxifen.
- He, Zhiheng,Kirchberg, Sylvia,Froehlich, Roland,Studer, Armido
-
supporting information; experimental part
p. 3699 - 3702
(2012/05/20)
-
- Tertiary alcohols by tandem β-carbolithiation and N→C aryl migration in enol carbamates
-
Enol carbamates (O-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and bearing an N-aryl substituent undergo carbolithiation by nucleophilic attack at the (nominally nucleophilic) β position of the enol double bond. The resulting carbamate-stabilized allylic, propargylic, or benzylic organolithium rearranges with N→C migration of the N-aryl substituent, creating a quaternary carbon α to O. The products may be readily hydrolyzed to yield multiply branched tertiary alcohols in a one-pot tandem reaction, effectively a polarity-reversed nucleophilic β-alkylation-electrophilic α-arylation of an enol equivalent.
- Fournier, Anne M.,Clayden, Jonathan
-
p. 142 - 145
(2012/02/14)
-
- 2,2-(Diaryl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst
-
A novel 2,2-(diaryl)vinylphosphine compound represented by the following general formula (1): (wherein R1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc.; R2, R3, R4, R5, R6, and R7 may be the same or different and each is an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc., provided that R4 and R5 taken together and/or R6 and R7 taken together may represent a fused benzene ring, a substituted fused benzene ring, a trimethylene group, etc.; and p, q, r, and s each is 0 to 5, provided that p+q and r+s each is in the range of from 0 to 5); a palladium-phosphine catalyst obtained by causing a palladium compound to act on the novel 2,2-(diaryl)vinylphosphine compound; and a process for obtaining an arylamine, a diaryl and an arylalkyne in the presence of the palladium-phosphine catalyst.
- -
-
-
- One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
-
The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78 deg C, affords diarylalkylcarbinols in good yields.Alkyl chlorides do not react under similar experimental conditions.This feature makes the reaction particularly useful for the synthesisof alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols.The procedure can also be adapted to afford substituted cyclic ethers.If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful intermediates.With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields.
- Vitale, Arturo A.,Doctorovich, F.,Nudelman, N. Sbarbati
-
-