Synthesis of Rhodamines from Fluoresceins Using Pd-Catalyzed C–N Cross-Coupling

نویسندگان

  • Jonathan B. Grimm
  • Luke D. Lavis
چکیده

A unified, convenient, and efficient strategy for the preparation of rhodamines and N,N'-diacylated rhodamines has been developed. Fluorescein ditriflates were found to undergo palladium-catalyzed C-N cross-coupling with amines, amides, carbamates, and other nitrogen nucleophiles to provide direct access to known and novel rhodamine derivatives, including fluorescent dyes, quenchers, and latent fluorophores.

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

General Synthetic Method for Si-Fluoresceins and Si-Rhodamines

The century-old fluoresceins and rhodamines persist as flexible scaffolds for fluorescent and fluorogenic compounds. Extensive exploration of these xanthene dyes has yielded general structure-activity relationships where the development of new probes is limited only by imagination and organic chemistry. In particular, replacement of the xanthene oxygen with silicon has resulted in new red-shift...

متن کامل

Synthesis of Symmetrical Triaryl Amines by Nano-CuO Catalyzed Buchwald-Hartwig Cross-coupling Reaction: NH2-Thiadiazole as a New N-source

The one-pot synthesis of symmetrical triaryl amines using aryl halides and 5-Methyl-1,3,4-Thiadiazole-2-Amine as a nitrogen-transfer reagent is reported. Copper oxide nanoparticles that does not require the presence of any additional ligand, improved rate and facility of the synthesis of triaryl amines. The introduction of a new N-source, using green solvents PEG/H2O, normal atmospheric conditi...

متن کامل

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Pd-catalyzed cross-coupling reactions that form C-N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This r...

متن کامل

Facile and General Synthesis of Photoactivatable Xanthene Dyes**

Photoactivatable “caged” fluorophores enable numerous advanced biological imaging experiments, including photoactivated localization microscopy (PALM) and related super-resolution imaging techniques. Of the extant fluorophore scaffolds, caged rhodamines and fluoresceins display properties that are exceptionally well suited for superresolution microscopy, exhibiting high contrast and photon yiel...

متن کامل

SPION-A-Pd(EDTA) (superparamagnetic iron oxide nanoparticles-A-ethylendiamine tetraacetic acid) as a robust nanocatalyst for Buchwald-Hartwig C-N Coupling Reaction

During thelast20-30 years, palladium-catalyzed reactions have witnessed tremendous advances in the industrial and organic reactions such as hydrogenation, coupling, cyanation and amination. Despite the wide utility of Pd-catalysts in these reactions, they suffer from a number of drawbacks such as recovery, reuse of catalyst and remain as  a contaminant in the products at the end of the reaction...

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 13  شماره 

صفحات  -

تاریخ انتشار 2011