Visible light C-H amidation of heteroarenes with benzoyl azides.

نویسندگان

  • E Brachet
  • T Ghosh
  • I Ghosh
  • B König
چکیده

Benzoyl azides were used for the direct and atom economic C-H amidation of electron rich heteroarenes in the presence of phosphoric acid, a photocatalyst and visible light. Hetero-aromatic amides are obtained in good yields at very mild reaction conditions with dinitrogen as the only by-product. The reaction allows the use of aryl-, heteroaryl- or alkenyl acyl azides and has a wide scope for heteroarenes, including pyrroles, indole, furan, benzofuran and thiophene giving good regio-selectivities and yields.

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

Visible light C–H amidation of heteroarenes with benzoyl azides† †Electronic supplementary information (ESI) available: Characterization and synthesis of new compounds, general procedures, proton and carbon NMR spectra, crystal structure analysis, gas chromatographic analyses. CCDC 1017661. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02365j Click here for additional data file. Click here for additional data file.

Benzoyl azides were used for the direct and atom economic C–H amidation of electron rich heteroarenes in the presence of phosphoric acid, a photocatalyst and visible light. Hetero-aromatic amides are obtained in good yields at very mild reaction conditions with dinitrogen as the only by-product. The reaction allows the use of aryl-, heteroarylor alkenyl acyl azides and has a wide scope for hete...

متن کامل

N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C–H Amination of Arenes and Heteroarenes

This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aroma...

متن کامل

Iron(III) tetrakis(pentafluorophenyl)porpholactone catalyzes nitrogen atom transfer to C=C and C-H bonds with organic azides.

We have demonstrated that iron porpholactones could be effective catalysts for nitrogen atom transfer reactions such as aziridination of alkenes and amidation of alkanes using organic azides.

متن کامل

Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis

Although visible light photoredox catalysis has emerged as a powerful tool for the construction of C–C bonds, common catalysts and/or their photoexcited states suffer from low redox potentials, limiting their applicability to alkyl radical generation from substrates with activated carbon–halogen bonds. Radicals derived from these activated compounds, being highly electrophilic or stabilized, do...

متن کامل

Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

The direct α-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated CH functionalization pathway. Transiently generated α-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mil...

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:
  • Chemical science

دوره 6 2  شماره 

صفحات  -

تاریخ انتشار 2015