1361982-26-4Relevant academic research and scientific papers
Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
supporting information, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
Experimental and Computational Exploration of para-Selective Silylation with a Hydrogen-Bonded Template
Maji, Arun,Guin, Srimanta,Feng, Sheng,Dahiya, Amit,Singh, Vikas Kumar,Liu, Peng,Maiti, Debabrata
, p. 14903 - 14907 (2017/10/30)
The regioselective conversion of C?H bonds into C?Si bonds is extremely important owing to the natural abundance and non-toxicity of silicon. Classical silylation reactions often suffer from poor functional group compatibility, low atom economy, and insufficient regioselectivity. Herein, we disclose a template-assisted method for the regioselective para silylation of toluene derivatives. A new template was designed, and the origin of selectivity was analyzed experimentally and computationally. An interesting substrate–solvent hydrogen-bonding interaction was observed. Kinetic, spectroscopic, and computational studies shed light on the reaction mechanism. The synthetic significance of this strategy was highlighted by the generation of a precursor of a potential lipophilic bioisostere of γ-aminobutyric acid (GABA), various late-stage diversifications, and by mimicking enzymatic transformations.
Silanol as a removable directing group for the pdII-catalyzed direct olefination of arenes
Wang, Cong,Ge, Haibo
supporting information; experimental part, p. 14371 - 14374 (2012/01/19)
Need some direction? Silanol was developed as a directing group for the PdII-catalyzed oxidative Heck-type reaction of arenes. A one-pot C-H activation/desilylation process of benzyldiisopropylsilanol was also demonstrated, providing a powerful approach for the synthesis of ortho-alkenyl-substituted alkylarenes (see scheme). Considering the easily attachable and readily removable properties of the silanol group, this reaction will find broad synthetic applications.
