38382-35-3Relevant academic research and scientific papers
Regiodivergent C?H and Decarboxylative C?C Alkylation by Ruthenium Catalysis: ortho versus meta Position-Selectivity
Ackermann, Lutz,Korvorapun, Korkit,Messinis, Antonis M.,Moselage, Marc,Rogge, Torben,Struwe, Julia
supporting information, p. 18795 - 18803 (2020/08/27)
Ruthenium(II)biscarboxylate complexes enabled the selective alkylation of C?H and C?C bonds at the ortho- or meta-position. ortho-C?H Alkylations were achieved with 4-, 5- as well as 6-membered halocycloalkanes. Furthermore, the judicious choice of the directing group allowed for a full control of ortho-/meta-selectivities. Detailed mechanistic studies by experiment and computation were performed and provided strong support for an oxidative addition/reductive elimination process for ortho-alkylations, while a homolytic C?X cleavage was operative for the meta-selective transformations.
Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent
Zhang, Xinglu,Liu, Zhiqiang,Gao, Yu,Li, Feng,Tian, Yaming,Li, Chunju,Jia, Xueshun,Li, Jian
supporting information, p. 272 - 277 (2017/11/13)
A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).
Access to "friedel-Crafts-Restricted" tert -alkyl aromatics by activation/methylation of tertiary benzylic alcohols
Hartsel, Joshua A.,Craft, Derek T.,Chen, Qiao-Hong,Ma, Ming,Carlier, Paul R.
, p. 3127 - 3133 (2012/05/20)
Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
Aluminum Chloride Catalyzed Reaction of Acetanilide with Pivalyl Chloride
Maslak, Przemyslaw,Fanwick, Phillip E.,Guthrie, Robert D.
, p. 655 - 659 (2007/10/02)
Product development was studied in the aluminum chloride catalyzed reaction of acetanilide with pivalyl chloride. 3-tert-Butylacetanilide is the major product because of its relative resistance to dealkylation by reaction-produced HCl.At long reaction times all alkylation products are converted back to acetanilide with the only survivor being 2,2-dimethyl-5-tert-butyl-7-acetamidoindanone.The crystal structure of this compound was determined.It crystallized in the space group Pnma with cell constants a = 12.571 (3) Angstroem, b = 7.302 (1) Angstroem, c = 16.910 (3) Angstroem, V = 1552.24 Angstroem3, z = 4.Refinement of the 1224 data with F2 3?(F2) resulted in discrepancy indices R1 = 0.056 and R2 = 0.074.A novel mechanism for formation of this indanone is proposed, involving nucleophilic attack by alkene on a protonated arene ring.
