38382-35-3Relevant articles and documents
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.
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.