Palladium-Catalyzed Hydroboration/Cyclization of 1,n-Dienes

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Abstract

While the hydroboration of alkenes is well established, the corresponding cyclization reaction of dienes remains challenging. Here, we report a new method for hydroboration/cyclization applicable to various 1,n-dienes and hydroboranes. The method features the direct synthesis of borylalkyl cyclopentanes from common 1,6-dienes, which is highlighted by syntheses of elaborated pyrrolidine cores from easily accessible diallylamines. Notably, 1,n-dienes (n > 6) also undergo five-membered ring formation, offering “remote” hydroboration/cyclization that would be otherwise difficult to achieve.

Original languageEnglish
Pages (from-to)2621-2630
Number of pages10
JournalJournal of Organic Chemistry
Volume88
Issue number4
DOIs
Publication statusPublished - 2023 Feb 17

ASJC Scopus subject areas

  • Organic Chemistry

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