炔烃和烯炔的硼酯化。反应的范围和限制以及加合物的用途。
Borostannylation of alkynes and enynes. Scope and limitations of the reaction and utility of the adducts.
机构信息
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
出版信息
Org Lett. 2010 Jun 4;12(11):2622-5. doi: 10.1021/ol100824f.
Abstract
The utility of the hetero-bismetallating reagent 1,3-dimethyl-2-trimethylstannyl-2-bora-1,3-diazacyclopentane (1) has not been fully realized because of the hydrolytic instability of the products derived from catalyzed vicinal syn-additions to alkynes. The isolation of a variety of such adducts derived from alkynes (and also from hitherto unreported additions to 1,3-enynes) as stable boron pinacolates is reported. Examples of the applications of resulting products in tandem cross-coupling reactions and as dienes in Diels-Alder reactions are illustrated.
摘要
由于催化邻位顺式加成炔烃生成的产物水解不稳定，1,3-二甲基-2-三甲基锡基-2-硼-1,3-二氮杂环戊烷（1）这种杂双金属试剂的实用性尚未得到充分体现。本文报道了各种稳定的硼频哪醇酯类产物作为炔烃（以及 1,3-烯炔的未报道的加成产物）的加合物的分离。本文还举例说明了这些产物在串联交叉偶联反应中的应用，以及作为 Diels-Alder 反应中双烯的应用。
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