C–H functionalization of amines with aryl halides by nickel-photoredox catalysis† †Electronic supplementary information (ESI) available: Experimental details and characterization data. See DOI: 10.1039/c6sc02815b Click here for additional data file.

نویسندگان

  • Derek T. Ahneman
  • Abigail G. Doyle
چکیده

We describe the functionalization of α-amino C-H bonds with aryl halides using a combination of nickel and photoredox catalysis. This direct C-H, C-X coupling uses inexpensive and readily available starting materials to generate benzylic amines, an important class of bioactive molecules. Mechanistically, this method features the direct arylation of α-amino radicals mediated by a nickel catalyst. This reactivity is demonstrated for a range of aryl halides and N-aryl amines, with orthogonal scope to existing C-H activation and photoredox methodologies. We also report reactions with several complex aryl halides, demonstrating the potential utility of this approach in late-stage functionalization.

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

Photoredox mediated nickel catalyzed C(sp3)–H thiocarbonylation of ethers† †Electronic supplementary information (ESI) available: Experimental details and full characterization of substrates and products. Crystallographic data for compound [Ni-II]. CCDC 1516709. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02516e Click here for additional data file. Click here for additional data file.

The first direct C(sp)–H thiocarbonylation reaction is achieved by visible light photoredox/Ni dual catalysis. The thioester group of thiobenzoate is transferred to the a-oxy carbon of various cyclic/acyclic ethers, which is the opposite to the commonly expected chemical reactivity involving acyl group transfer via the weaker C(acyl)–S activation. Through mechanistic studies, we proposed that t...

متن کامل

Dual gold and photoredox catalysed C–H activation of arenes for aryl–aryl cross couplings† †Electronic supplementary information (ESI) available: Experimental procedures, full optimisation tables, control reaction, mechanistic studies, characterisation data and copies of NMR spectra of new compounds. See DOI: 10.1039/c6sc05469b Click here for additional data file.

A mild and fully catalytic aryl–aryl cross coupling via gold-catalysed C–H activation has been achieved by merging gold and photoredox catalysis. The procedure is free of stoichiometric oxidants and additives, which were previously required in gold-catalysed C–H activation reactions. Exploiting dual gold and photoredox catalysis confers regioselectivity via the crucial gold-catalysed C–H activa...

متن کامل

Photoredox ketone catalysis for the direct C–H imidation and acyloxylation of arenes† †Electronic supplementary information (ESI) available: Experimental procedures and characterization data for all relevant compounds. CCDC 1544882. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01700f Click here for additional data file. Click here for additional data file.

Acyloxylation of Arenes Chandra Bhushan Tripathi, Tsuyoshi Ohtani, Michael T. Corbett and Takashi Ooi*‡ Institute of Transformative Bio-Molecules (WPI-ITbM), ‡ Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan ‡CREST, Japan Science and Technology Agency (JST), Nagoya University, Nagoya 464-8601, Japan [email protected]...

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:

دوره 7  شماره 

صفحات  -

تاریخ انتشار 2016