Phosphoramidite accelerated copper(i)-catalyzed [3 + 2] cycloadditions of azides and alkynes.

نویسندگان

  • Lachlan S Campbell-Verduyn
  • Leila Mirfeizi
  • Rudi A Dierckx
  • Philip H Elsinga
  • Ben L Feringa
چکیده

Monodentate phosphoramidite ligands are used to accelerate the copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes (CuAAC) rapidly yielding a wide variety of functionalized 1,4-disubstituted-1,2,3-triazoles; Cu(i) and Cu(ii) salts both function as the copper source in aqueous solution to provide excellent 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

Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.

The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing div...

متن کامل

Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions.

This work represents our initial effort in identifying azide/alkyne pairs for optimal reactivity in copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. In previous works, we have identified chelating azides, in particular 2-picolyl azide, as "privileged" azide substrates with high CuAAC reactivity. In the current work, two types of alkynes are shown to undergo rapid CuAAC reactions u...

متن کامل

Copper(I)–Phosphinite Complexes in Click Cycloadditions: Three‐Component Reactions and Preparation of 5‐Iodotriazoles

The remarkable activity displayed by copper(I)-phosphinite complexes of general formula [CuBr(L)] in two challenging cycloadditions is reported: a) the one-pot azidonation/cycloaddition of boronic acids, NaN3, and terminal alkynes; b) the cycloaddition of azides and iodoalkynes. These air-stable catalysts led to very good results in both cases and the expected triazoles could be isolated in pur...

متن کامل

FULL PAPER Copper(I)‒Phosphinite Complexes in Click Cycloadditions: Three- Component Reactions and Preparation of 5-Iodotriazoles

The remarkable activity displayed by copper(I)phosphinite complexes of general formula [CuBr(L)] in two challenging cycloadditions is reported: a) the one pot azidonation/cycloaddition from boronic acids, NaN3 and terminal alkynes; b) the cycloaddition of azides and iodoalkynes. These airstable catalysts led to very good results in both cases and the expected triazoles could be isolated pure un...

متن کامل

Gold-Catalyzed Synthesis of Tetrazoles from Alkynes by C=C Bond Cleavage**

Cycloadditions of azides with alkynes to form triazoles under thermal conditions (Huisgen cycloaddition) or in the presence of copper [click reaction, copper-catalyzed azide– alkyne cycloaddition (CuAAC)] are reactions of fundamental importance in organic chemistry. Triazoles can also be obtained by means of ruthenium, silver, and iridium catalysis, as well as by a zinc-mediated process. In sha...

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 communications

دوره 16  شماره 

صفحات  -

تاریخ انتشار 2009