Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• -dibromothienothiophene 2 [39], which was obtained from thieno[3,2-b]thiophene (1) [38], was triisopropylsilyl (TIPS)-protected by lithium-halogen exchange with n-BuLi and triisopropylsilyl chloride to give thienothiophene 3 in 69% yield. A halogen dance reaction of 3, induced by lithium diisopropylamide (LDA) at −78 °C

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

• Jessica Matthias,
• Thines Kanagasundaram,
• Klaus Kopka and
• Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

• optical properties for medical and bioimaging. As a compound with intrinsic mitochondria targeting ability, the radiolabelled analogue can be applied in multimodal (PET/OI) imaging of mitochondria for diagnostic and therapeutic use in, e.g., cancer patients. Keywords: halogen-dance reaction

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• -coupling/cyclization reactions, respectively. In both cases, the synthesis started from TMS-protected diiodinated 2,2’-biselenophene 11, which was prepared from 2-iodo-5-(trimethylsilyl)selenophene (10) in 59% yield by lithiation with LDA, halogen-dance reaction [34], and subsequent oxidative