252863-69-7Relevant academic research and scientific papers
Synthesis of novel quinone boronic ester derivatives via a highly regioselective Cr-mediated benzannulation reaction and their application in Pd-catalyzed coupling processes
Davies,Johnson,Harrity
, p. 3525 - 3532 (2007/10/03)
This paper describes the synthesis and reactivity of a novel class of quinone boronic esters. These compounds are prepared utilizing a highly regioselective Doetz annulation of Fischer carbene complexes with alkynylboronates. All substrates studied to date provided a single regioisomeric arylboronic ester product; the origin of this selectivity is discussed in the context of steric and electronic effects. Additionally, these compounds have been found to undergo Pd-catalyzed coupling reactions with a range of aryl and allyl halides and provides a strategy for the selective and predictable preparation of highly substituted quinones and hydroquinones. Finally, the propensity of this technique to prepare highly functionalized aromatic compounds in an expeditious fashion is demonstrated in the total synthesis of dimeric carbazole (±)-bis-N-dimethylbismurrayaquinone-A 33.
A novel and highly regioselective Cr-mediated route to functionalised quinone boronic ester derivatives
Davies, Mark W.,Johnson, Christopher N.,Harrity, Joseph P. A.
, p. 2107 - 2108 (2007/10/03)
A novel and highly regioselective route to quinone boronic ester derivatives has been developed using a Fischer carbene mediated benzannulation process.
