Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes | Zendy

Carlotta Figliola | Zendy; Katherine N. Robertson | Zendy; Sarah M. Greening | Zendy; Alison Thompson | Zendy

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Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes

Author(s) -

Carlotta Figliola,

Katherine N. Robertson,

Sarah M. Greening,

Alison Thompson

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b01129

Subject(s) - chemistry , sonogashira coupling , alkyne , conjugated system , substituent , electrophile , enol , reactivity (psychology) , stereochemistry , organic chemistry , palladium , catalysis , polymer , medicine , alternative medicine , pathology

An asymmetric meso-H dipyrrin featuring a conjugated terminal alkyne substituent was converted to its corresponding difluoro boron complex, and the extent of π-conjugation was extended using Sonogashira cross-coupling. Treatment of the alkyne-substituted dipyrrin with BF 3 ·OE 2 and NE 3 revealed the reactivity of the conjugated terminal alkyne toward Lewis-activated electrophilic substitution and led to the isolation of F-BODIPYs bearing terminal bromovinyl and enol substituents.

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