31930-34-4Relevant articles and documents
Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity
Ivon, Yevhen M.,Kuchkovska, Yuliya O.,Voitenko, Zoya V.,Grygorenko, Oleksandr O.
, p. 3367 - 3377 (2020/03/13)
A protocol for the preparation of α-boryl-α-bromoketones from alkenyl MIDA boronates was developed and applied to functionalized aliphatic derivatives. The reaction sequence included regioselective hydroxybromination of olefin moiety, followed by oxidation of alcohol group with Dess–Martin periodinane. The target trifunctional boronate-containing derivatives were obtained in up to 94 % yield over two steps starting from alkenyl MIDA boronates. In some cases, functional groups present in the substrate participated in the bromohydroxylation step via intramolecular nucleophilic attack at the bromonium cation leading to cyclic products. Additionally, the reactivity of aliphatic α-boryl-α-bromoketones was illustrated by nucleophilic substitution at the α-C atom and heterocyclization reactions.
Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes
Fuentespina, Ruben Pomar,De La Cruz, José Angel Garcia,Durin, Gabriel,Mamane, Victor,Weibel, Jean-Marc,Pale, Patrick
supporting information, p. 1416 - 1424 (2019/07/10)
1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.
Palladium-catalyzed intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides
Shen, Zengming,Ni, Zhenjie,Mo, Song,Wang, Jing,Zhu, Yamin
supporting information; experimental part, p. 4859 - 4865 (2012/06/04)
Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad. Copyright
