27983-08-0Relevant academic research and scientific papers
Decarboxylative Bromination of Sterically Hindered Carboxylic Acids with Hypervalent Iodine(III) Reagents
Kanazawa, Junichiro,Koyamada, Kenta,Miyamoto, Kazunori,Uchiyama, Masanobu,Watanabe, Ayumi
supporting information, p. 1328 - 1334 (2020/08/14)
Sterically hindered three-dimensional (3D) alkyl halides are promising precursors for various reactions; however, they are difficult to synthesize via conventional reactions. We present an efficient and practical method for decarboxylative bromination of sterically hindered 3D aliphatic carboxylic acids using commercially available (diacetoxyiodo)benzene and potassium bromide, one of the most stable and cheapest bromine sources in nature. The present method features a metal-free/Br2-free system, mild reaction conditions, one-pot operation under air at room temperature, wide functional group compatibility, and gram-scale synthetic capability. This highly efficient reaction cleanly converts a broad range of carboxylic acids, the most inexpensive and readily available sources of highly strained/naturally occurring/drug-related scaffolds, into the corresponding alkyl bromides in good to high yields.
Azido-Adamantyl Tin Sulfide Clusters for Bioconjugation
Berndt, Jan-Philipp,Engel, Annikka,Hrdina, Radim,Dehnen, Stefanie,Schreiner, Peter R.
supporting information, p. 329 - 335 (2019/02/01)
We present a new versatile route toward biomolecule-functionalized tin sulfide clusters. A novel bifunctional orthogonal spacer was developed and used for the formation of a trifold azido-adamantyl-terminated cluster, serving as a building block for click reactions. The azido cluster was quantitatively bioconjugated via a strain-promoted 1,3-dipolar cycloaddition, affording a peptide-decorated cluster.
Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions
Yoshida, Suguru,Nonaka, Takako,Morita, Takamoto,Hosoya, Takamitsu
supporting information, p. 7489 - 7493 (2014/12/11)
A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-medi
Synthese de quelques structures encombrees derivees de l'adamantane et de ses analogues par alkylation des ether d'enol trimethylsilyliques
Dubois, Jacques-Emile,Lebbar, Kadija,Lion, Claude,Dugast, Jean-Yves
, p. 905 - 910 (2007/10/02)
Alkylation of trimethylsilyl enol ethers of 2,4-dimethyl-3-pentanone, cyclopentanone and cyclohexanone has been extended to alkylating agents with a cage structure (substituted or functionalized adamantyl, diamantyl, homoadamantyl and noradamantyl chlorides or bromides).This method affords some new cage structured aliphatic and alicyclic ketones.In some cases one observes a new TiCl4 promoted reaction where the bromine in the alkylating agent is replaced by chlorine.This work is a generalization of our previous extended studies on α-alkylation of ketones with tertiary alkylating agents.
Herstellung und Solvolyse von 3-substituierten p-Toluolsulfonsaeure-(1-adamantyl)estern
Bielman, Rolf,Grob, Cyril A.,Schaub, Bruno
, p. 1728 - 1733 (2007/10/02)
Methods for the preparation of some hitherto unknown 3-substituted 1-adamantyl toluenesulfonates are evaluated.Their solvolysis products in dioxane/water 70:30 are reported.
