Conversion of F-BODIPYs to Cl-BODIPYs: enhancing the reactivity of F-BODIPYs.

نویسندگان

  • Travis Lundrigan
  • Alison Thompson
چکیده

A new method for the synthesis of Cl-BODIPYs from F-BODIPYs is reported, merely requiring treatment of the F-BODIPY with boron trichloride. Cl-BODIPYs are exploited as synthetic intermediates generated in situ for the overall conversion of F-BODIPYs to O- and C-BODIPYs in high overall yields using a mild one-pot procedure. This route enables F-BODIPYs to be transformed into derivatives that are not accessible via the direct route, as demonstrated via the use of 1,3-propanediol.

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

Cl-BODIPYs: a BODIPY class enabling facile B-substitution.

Cl-BODIPYs, synthesized in high yields from dipyrrins under air- and moisture-free conditions, are extremely facile to substitution at boron compared to their corresponding F-BODIPYs, opening up a new route to BODIPYs functionalized at boron.

متن کامل

Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives.

A high-yielding method for the direct thiocyanation of BODIPY dyes is described. In 1,3-dimethyl BODIPYs, the thiocyanato group adds at position 2, whereas the insertion occurs at position 5 in 3-amino BODIPYs. The transformation of the thiocyanato group enables the synthesis of thioalkylated BODIPYs. 2-Thioalkylated BODIPYs and 3-thiocyanato-5-piperidino BODIPYs exhibit interesting spectroscop...

متن کامل

Activation and deprotection of F-BODIPYs using boron trihalides.

The activation of F-BODIPYs with boron trihalides, followed by treatment with a nucleophile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the -BF2 moiety and thereby production of the corresponding parent dipyrrin salt in quantitative yield under extremely mild conditions.

متن کامل

Meso enyne substituted BODIPYs: synthesis, structure and properties.

We report the synthesis of meso enyne substituted BODIPYs by the reaction of 8-chloro BODIPY with terminal alkynes under Sonogashira coupling conditions, and by Pd-Cu catalyzed hydroalkynylation reaction of terminal alkynes, across the -C[triple bond, length as m-dash]C- bond of meso alkynylated BODIPYs. The scope of reaction was explored by reacting different meso alkynylated BODIPYs with vari...

متن کامل

Bridged bis-BODIPYs: their synthesis, structures and properties.

A series of bis-BODIPYs 1-6 bridged via thiophene, furan, N-alkylcarbazole, triphenyl-amine, para- and meta-phenylene groups have been synthesized and characterized by various spectroscopic techniques. The change in the spectroscopic properties of bis-BODIPYs upon varying the size of spacers was studied. X-ray crystal structures of three bis-BODIPYs containing triphenylamine, para- and meta-phe...

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:
  • The Journal of organic chemistry

دوره 78 2  شماره 

صفحات  -

تاریخ انتشار 2013