76499-94-0Relevant academic research and scientific papers
One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines
Chand-Thakuri, Pratibha,Landge, Vinod G.,Kapoor, Mohit,Young, Michael C.
supporting information, p. 6626 - 6644 (2020/07/14)
An efficient method has been developed for the synthesis of seven-membered biaryl lactams involving Pd-catalyzed, native amine-directed, ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized coupling partner is also explored, as is the potential for synthesizing eight-membered biaryl lactams. Various applications are also investigated, including access to the aza-brassinolide core.
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.
experimental part, 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.
New ligands and structural insights into the catalytic asymmetric addition of organozinc reagents to ketones
Huelgas, Gabriela,Larochelle, Lynne K.,Rivas, Lucrecia,Luchinina, Yekaterina,Toscano, Rubén A.,Carroll, Patrick J.,Walsh, Patrick J.,Anaya De Parrodi, Cecilia
experimental part, p. 4467 - 4474 (2011/08/04)
The catalytic asymmetric addition of alkyl groups to ketones has received considerable attention. Outlined herein is the synthesis of two new ligands based on the C2-symmetric 11,12-diamino-9,10-dihydro-9,10- ethanoanthracene. The scope of the new ligands has been evaluated in the catalytic asymmetric addition of diethylzinc to a variety of ketones. Enantioselectivities as high as 99% have been achieved. The structures of two of these ligands have been determined by X-ray crystallography and are compared with related structures. Additionally, the structure of a titanium complex bound to a bis(sulfonamide) diol ligand is reported.
The Importance of Resonance Stabilization in the Benzylic Solvolysis. Substituent Effects on the Solvolysis of α,α-Diisopropylbenzyl Chlorides
Fujio, Mizue,Nakata, Kazuhide,Kuwamura, Takashi,Nakamura, Hirotaka,Saeki, Yoshihiro,et al.
, p. 8309 - 8312 (2007/10/02)
The substituent effect on the solvolysis of α,α-diisopropylbenzyl chlorides can be described in terms of ?+ value.No significant steric loss of resonance was observed by introducing two bulky isopropyl groups into benzylic reaction center.
