1291101-64-8

Upstream product

• 591-51-5 phenyllithium 

Relevant academic research and scientific papers

Investigations into the nucleophilic meso-substitution of f-bodipys and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

A series of three F-BODIPYs, with varying levels of steric crowding about the meso-position were selected to investigate nucleophilic meso-substitution of F-BODIPYs. The synthesis of one of these F-BODIPYs, 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene (totally unsubstituted dipyrrin skeleton), was optimized to give higher yields over routine literature procedures. This modified procedure involves oxidation of a dipyrromethane using p-chloranil, instead of DDQ, to give a dipyrrin which is then trapped in situ as its BF2 complex. Nucleophilic meso-alkylation of the series of F-BOIDPYs with n-butyllithium gave meso-butyl F-BODIPYs in moderate to good yields. This work represents a new, synthetically viable method for the synthesis of meso-alkylated F-BODIPYs. Extension of the nucleophilic substitution methodology to meso-arylation was possible. However, the reaction was unselective: substitution at boron, to give the boron-diaryl C-BOIDPYs, occurred preferentially to nucleophilic meso-substitution and thus a mixture of products was obtained. The Japan Institute of Heterocyclic Chemistry.

Conversion of 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacenes (F-BODIPYs) to dipyrrins with a microwave-promoted deprotection strategy

Chemical eqation presented 4,4-Difluoro-4-bora-3a,4a-diaza-s- indacenes (F-BODIPYs) have been deprotected to give the corresponding free-base dipyrrins by heating a solution of the F-BODIPY in tert-butanol under 600 W of microwave irradiation in the presence of 6 equiv of potassium tert-butoxide for 40 min at 92 C. Investigations of BODIPY modification at the meso position have also been undertaken and a meso-butyl product has been isolated.