Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives

The Journal of Organic Chemistry
Andrea SavoldelliM Graça H Vicente

Abstract

A novel route for the synthesis of unsymmetrical benzo-fused BODIPYs is reported using 4,5,6,7-tetrafluoroisoindole as a precursor. The reactivity of the 3,5-dibromo tetrafluorobenzo-fused BODIPY was investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling reaction conditions. In addition to the 3,5-bromines, one α-fluoro group on the benzo-fused ring can also be functionalized, and an unusual homocoupling with formation of a bisBODIPY was observed. This new class of fluorinated BODIPYs could find various applications in medicine and materials.

References

May 7, 2005·The Journal of Organic Chemistry·Mukulesh BaruahNoël Boens
Sep 1, 2005·Journal of the American Chemical Society·Takatoshi YogoTetsuo Nagano
Jan 5, 2006·Journal of the American Chemical Society·Li ZengChristopher J Chang
Jan 5, 2006·Chemical Communications : Chem Comm·Taoufik RohandWim Dehaen
Oct 5, 2007·The Journal of Organic Chemistry·Zaiguo Li, Robert Bittman
Oct 11, 2007·Chemical Reviews·Aurore Loudet, Kevin Burgess
Nov 27, 2007·Bioorganic & Medicinal Chemistry Letters·Lingling LiKevin Burgess
Dec 20, 2007·Angewandte Chemie·Gilles UlrichAnthony Harriman
Feb 29, 2008·Chemistry : a European Journal·Martin BröringLucia Flamigni
Mar 1, 2008·Chemical Communications : Chem Comm·Jinling SongWendong Sun
Jun 5, 2008·The Journal of Organic Chemistry·Mingjian YuanDaoben Zhu
Sep 26, 2008·Chemical Communications : Chem Comm·Todd W Hudnall, François P Gabbaï
Oct 22, 2008·Chemical Communications : Chem Comm·Liangxing Wu, Kevin Burgess
Dec 17, 2008·Organic & Biomolecular Chemistry·Junyan HanKevin Burgess
Mar 19, 2009·Chemical Communications : Chem Comm·Theodulf RousseauJean Roncali
May 22, 2009·Tetrahedron·Aurore LoudetKevin Burgess
Jul 21, 2009·Chemical Communications : Chem Comm·Volker LeenWim Dehaen
Mar 5, 2010·Journal of Medicinal Chemistry·Siang Hui LimHong Boon Lee
Mar 23, 2010·Angewandte Chemie·Neal K DevarajRalph Weissleder
Apr 15, 2010·Organic & Biomolecular Chemistry·Lijuan JiaoM Graça H Vicente
Mar 26, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Jiping YangYen Wei
May 20, 2011·Organic Letters·Yosuke HayashiHiroshi Shinokubo
Jul 29, 2011·Chemical Society Reviews·Noël BoensWim Dehaen
Sep 14, 2011·The Journal of Organic Chemistry·Vellanki Lakshmi, Mangalampalli Ravikanth
Oct 4, 2011·Tetrahedron Letters·Amit AggarwalCharles Michael Drain
Nov 15, 2011·The Journal of Organic Chemistry·Lijuan JiaoErhong Hao
Feb 16, 2012·Photochemistry and Photobiology·Joana B PereiraJoão P C Tomé
Mar 1, 2012·Chemistry : a European Journal·Timsy UppalM Graça H Vicente
Mar 31, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·V Lakshmi, M Ravikanth
Apr 21, 2012·Chemistry : a European Journal·Changjiang YuErhong Hao
May 24, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jianguang WangXuesong Wang
Jun 26, 2012·Angewandte Chemie·Changjiang YuErhong Hao
Sep 28, 2012·Chemical Society Reviews·Anyanee KamkaewKevin Burgess
Jun 20, 2014·Chemical Communications : Chem Comm·Leandro M O LourençoJoão P C Tomé
Oct 1, 2014·The Journal of Organic Chemistry·Haijun WangKevin M Smith
Mar 17, 2015·Journal of Photochemistry and Photobiology. B, Biology·Jaime H GibbsM Graça H Vicente
Mar 25, 2015·Chemical Society Reviews·Toshiyuki KowadaKazuya Kikuchi
Sep 16, 2015·Chemical Communications : Chem Comm·Aaron MartinTia E Keyes

❮ Previous
Next ❯

Citations

Sep 14, 2019·Chemistry : a European Journal·Edurne Avellanal-ZaballaJ Cristobal Lopez
Jun 12, 2019·Chemistry : a European Journal·Maria I Martinez EspinozaFrancesca Baldelli Bombelli
Nov 9, 2021·The Journal of Organic Chemistry·Wanwan LiLijuan Jiao

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Beilstein Journal of Organic Chemistry
Frederik DinessMikael Begtrup
Chemical Communications : Chem Comm
Travis LundriganAlison Thompson
The Journal of Organic Chemistry
Lijuan JiaoKevin M Smith
© 2022 Meta ULC. All rights reserved