Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent.

نویسندگان

  • Leonardo Degennaro
  • Marina Zenzola
  • Piera Trinchera
  • Laura Carroccia
  • Arianna Giovine
  • Giuseppe Romanazzi
  • Aurelia Falcicchio
  • Renzo Luisi
چکیده

The regioselective lithiation-functionalization of 2-arylazetidines has been explored. The nature of the N-substituent is mainly responsible for a regioselectivity switch. ortho-Lithiation occurred, using hexyllithium as a greener base, in N-alkylazetidines, while α-benzylic lithiation has been observed with N-Boc azetidines.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

The phenomenology of place and Space in Theater stage According to Norberg Schulz Case study: Directing of Elinstein on the Beach by Robert Wilson

Theater and architecture create space and the spirit of life through settings, and both possess the nature of movement, time, rhythm, light, and color. Space and time are the most important common elements of these two arts. Theater directors and designers can put on meaningful and identity- based performances if they make organic use of the human-space relationship in creating space. Phenomeno...

متن کامل

Theoretical insight of substituent effect in para substituted Fe(CO)4–pyridine complexes

Abstract: Systematic studies on the substituent effect in para substituted Fe(CO)4–pyridine complexes have been studied on the basis of DFT quantum-chemical calculations. The following substituents were taken into consideration: NO2, CN, CHO, F, H, CH3, and OH. Additionally, the Fe–N and Fe–C bonds were characterized on the basis of Atoms in Molecules topological analysis of electron density. I...

متن کامل

The directing group wins over acidity: kinetically controlled regioselective lithiation for functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives.

Regioselective lithiation followed by functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives with different electrophiles was achieved in good to excellent yields. When the title compound is treated with n-butyl lithium, lithiation occurs selectively at the aromatic carbon having less acidic proton despite the presence of thermodynamically more acidic 1,3-dithiane proton in the same...

متن کامل

Palladium(II)-Catalyzed Regioselective Ortho Arylation of sp2 C—H Bonds of N-Aryl-2-amino Pyridine Derivatives

The direct arylation of N-(2-pyridyl) substituted anilines is described. Arylation takes place in ortho position to the amine functionality and is directed by the pyridine N-substituent. Remarkably, N-arylation was never observed as a competing process even though conditions also suitable for Buchwald-Hartwig reactions were applied. The scope of the reaction was investigated in terms of aryl do...

متن کامل

Ortho-phenylenediamine Based Bis-ureas as the Ion Selective Sensors; A QM/MD Study

Density functional theory dispersion corrected (DFT-D3)calculations and molecular dynamic (MD) simulation were applied to investigate the sensing ability of four types of receptors (RCs) composed of the ortho-phenylenediamine based bis-ureas for selective complexation with the anions such as Cl–, Br–, OAC–, PhCO2–, H2PO4– and HSO4– in the gas phase and DMSO. On the basis of the data obtained fr...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Chemical communications

دوره 50 14  شماره 

صفحات  -

تاریخ انتشار 2014