Gold-catalyzed α-furanylations of quinoline N-oxides with alkenyldiazo carbonyl species.

نویسندگان

  • Vinayak Vishnu Pagar
  • Rai-Shung Liu
چکیده

Gold-catalyzed α-furanylations of 8-alkylquinoline N-oxides have been achieved using alkenyldiazo carbonyl species as nucleophiles. The reactions are applicable to a reasonable range of alkenyldiazo species and 8-alkylquinoline N-oxides. The reaction mechanism is postulated to involve an initial nucleophilic addition of diazocarbonyl species at 8-alkylquinoline N-oxides, followed by diazo decomposition.

برای دانلود 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

A Non-Diazo Approach to α-Oxo Gold Carbenes via Gold-Catalyzed Alkyne Oxidation

For the past dozen years, homogeneous gold catalysis has evolved from a little known topic in organic synthesis to a fully blown research field of significant importance to synthetic practitioners, due to its novel reactivities and reaction modes. Cationic gold(I) complexes are powerful soft Lewis acids that can activate alkynes and allenes toward efficient attack by nucleophiles, leading to th...

متن کامل

Palladium-Catalyzed C8-Selective C–H Arylation of Quinoline N-Oxides: Insights into the Electronic, Steric, and Solvation Effects on the Site Selectivity by Mechanistic and DFT Computational Studies

We report herein a palladium-catalyzed C-H arylation of quinoline N-oxides that proceeds with high selectivity in favor of the C8-isomer. This site-selectivity is unusual for palladium, since all of the hitherto described methods of palladium-catalyzed C-H functionalization of quinoline N-oxides are highly C2-selective. The reaction exhibits a broad synthetic scope with respect to quinoline N-o...

متن کامل

Gold-catalyzed diastereoselective [2+2+2]-cycloaddition of 1,7-enynes with carbonyl compounds.

We report a gold-catalyzed [2+2+2]-cycloaddition of 1,7-enynes with carbonyl species; our experimental data suggest that the resulting oxacyclic cycloadducts arose from an interception of gold-containing cyclobutenium intermediates with carbonyl species.

متن کامل

Construction of cyclic enones via gold-catalyzed oxygen transfer reactions

During the last decade, gold-catalyzed reactions have become a tour de force in organic synthesis. Recently, the gold-, Brønsted acid- or Lewis acid-catalyzed oxygen transfer from carbonyl to carbon-carbon triple bond, the so-called alkyne-carbonyl metathesis, has attracted much attention because this atom economical transformation generates α,β-unsaturated carbonyl derivatives which are of gre...

متن کامل

Catalytic asymmetric construction of tetrasubstituted carbon stereocenters by conjugate addition of dialkyl phosphine oxides to β,β-disubstituted α,β-unsaturated carbonyl compounds.

The catalytic asymmetric phospha-Michael reaction of dialkyl phosphine oxides with β,β-disubstituted α,β-unsaturated carbonyl compounds was achieved. The products bearing tetrasubstituted carbon stereocenters were obtained in high yields with excellent enantioselectivities (up to >99% ee).

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

برای دانلود 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

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 13 22  شماره 

صفحات  -

تاریخ انتشار 2015