Atom-economical group-transfer reactions with hypervalent iodine compounds

• Andreas Boelke,
• Peter Finkbeiner and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

• –Hagihara reaction was developed by Dauban and co-workers (Scheme 16) [47]. The first step of this sequence includes an iodine(III)-mediated rhodium-catalysed enantioselective amination of an unactivated C(sp3)–H bond with a chiral sulfonimidamide 31. Afterwards, the iodoarene byproduct of the first step is

• incorporated into the final product, the calculated AE (46% for R1 = R2 = H, R3 = Ar = Ph) is close to the procedures of Panda and Xie due to lower PIDA loadings. A metal-catalysed procedure for the atom-economical utilization of (dicarboxyiodo)benzenes 20 in a tandem C(sp3)–H amination/sila-Sonogashira

The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles

• Joscha Vollmeyer,
• Ute Baumeister and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 910–920, doi:10.3762/bjoc.10.89

• Supporting Information File 1). Then 6 is attached to 5 in a fourfold Sonogashira–Hagihara reaction. To compensate the acetylene dimerization side reaction, the acetylene is added in 25% excess. Fluoride-induced removal of the silyl protecting groups yields the precursor 7. With Pd(PPh3)2Cl2 and CuI as

Synthesis of diverse indole libraries on polystyrene resin – Scope and limitations of an organometallic reaction on solid supports

• Kerstin Knepper,
• Sylvia Vanderheiden and
• Stefan Bräse

Beilstein J. Org. Chem. 2012, 8, 1191–1199, doi:10.3762/bjoc.8.132

• dried in high vacuum. The loading of the resulting resin was calculated as if complete conversion had taken place. GP 4 - Sonogashira–Hagihara reaction: Under an argon atmosphere, one equiv of the respective 7-bromo-1H-indole-6-carboxymethyl-polystyrene is suspended in DMF (0.1 mmol/mL) together with

• indole 3{h,d} and methyl 3-amino-4-chlorobenzoate (aniline): Isolated yields. Diverse synthesis of indoles using Bartoli reactions. aSee [24]. Stille reaction on solid supports. Suzuki reaction on solid supports. Sonogashira–Hagihara reaction on solid supports. Cleavage of indoles from solid supports

Sonogashira–Hagihara reactions of halogenated glycals

• Dennis C. Koester and
• Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

• Dennis C. Koester Daniel B. Werz Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany 10.3762/bjoc.8.75 Abstract Herein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated

• substituent in position 2. Keywords: C-glycosides; enyne; glycals; reductive/oxidative refunctionalization; Sonogashira–Hagihara reaction; Introduction Carbohydrates are key players in a plethora of biological processes, such as cell-development, metastasis, cell–cell aggregation and viral infection [1][2

• been no in-depth study of the synthesis of 1- and 2-alkynylated glycals by means of the Sonogashira–Hagihara reaction to date. Herein, we wish to report on our findings with respect to the reaction of persilylated 1-iodoglucal 7 and peracetylated 2-bromogalactal 10 with readily available alkynes 8a–8h