Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst

نویسندگان

  • Niki R. Patel
  • Christopher B. Kelly
  • Allison P. Siegenfeld
  • Gary A. Molander
چکیده

An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are subsequently engaged in a C-C bond-forming reaction with imines. The process is highly selective, metal-free, and does not require a large excess of the alkylating reagent or the use of acidic additives.

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

Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation.

Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe)2]2 and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% e...

متن کامل

Stereo- and Regio-specificity in Organic Synthesis Promoted by Metal Ions

This paper examines regio-and stereo-specificity for reactions of coordinated organic substrates. The reactions involve addition of coordinated nucleophiles where the specificity arises from non-bonded interactions, substituent effects on the metal, orbital steering directed by the chelates and electronic effects imparted by the geometry required for chelation. The reactions examined include hy...

متن کامل

Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02653b Click here for additional data file.

A photoredox-mediated Minisci C–H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, ...

متن کامل

Pd-catalyzed asymmetric allylic alkylations via C-H activation of N-allyl imines with glycinates.

Herein is reported the first example of palladium-catalyzed asymmetric allylic alkylation (AAA) reactions involving 2-aza-π-allyl palladium intermediates. The 2-aza-π-allyl complex was generated via a novel mode of activation of N-allyl imines. Pd-catalyzed C(sp3)-H activation of N-allyl imines and subsequent nucleophilic attack by glycinates delivered vicinal diamino derivatives as the sole re...

متن کامل

FeCl3-promoted alkylation of indoles by enamides.

An efficient iron-promoted alkylation of indoles with enamides has been accomplished under mild reaction conditions. The reaction proceeded with remarkable regioselectivity leading exclusively to substitution by indoles at α-position of enamides.

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 2017