Selective synthesis of organoboron compounds with copper(i)-phosphine complex catalysts

Eiji Yamamoto, Yuta Takenouchi, Koji Kubota, Hajime Ito

Research output: Contribution to journalReview article

1 Citation (Scopus)

Abstract

Transition-metal-catalyzed borylation has emerged as a powerful method for preparation of organoboron compounds, which are useful synthetic reagents in organic synthesis. However, chemo-, regio-, and stereoselective synthesis of the boron compounds are still highly required. Herein, we report copper (I)-catalyzed boryl substitution of allylic carbonates and ethers, monoborylation of 1,3-dienes and enynes, boryl substitution of alkyl halides, and borylative cyclization of alkenes containing an appropriate leaving group for the selective synthesis of various organoboron compounds including allyl- and allenylboronales, and optically active carbocyclic boronates. Preparation of the borylation products has been difficult with known procedures. In addition, direct enantio-convergent transformation of racemic substrates without a racemization or symmelrization process, a novel methodology for asymmetric synthesis with racemic substrates, is also reported.

Original languageEnglish
Pages (from-to)758-769
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume72
Issue number7
DOIs
Publication statusPublished - Jul 1 2014
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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