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Direct Carboboration of Aryl Alkenes with Stable Organoborons Through Ziegler‐Type Addition

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Bibliographic Details
Title: Direct Carboboration of Aryl Alkenes with Stable Organoborons Through Ziegler‐Type Addition
Authors: Mo Yang, Shengda Chen, Daojing Li, Liuzhou Gao, Guoqiang Wang, Shuhua Li
Source: Advanced Science, Vol 12, Iss 43, Pp n/a-n/a (2025)
Publisher Information: Wiley, 2025.
Publication Year: 2025
Collection: LCC:Science
Subject Terms: boron, carboboration, carbometalation, density functional calculations, Ziegler addition, Science
Description: Abstract Carbometallation reaction represents a classic strategy for the bifunctionalization of unsaturated hydrocarbons, yet conventional implementations predominantly rely on either highly reactive organometallic reagents or transition metal catalysts. Notably, the direct employment of metalloid organoboron reagents for such addition processes remains elusive except when specific substrate combinations are employed. Herein, a base‐catalyzed carboboration reaction of aryl alkenes with bench‐stable benzylic boronates is reported. This anionic‐based strategy is not only applicable to the carboboration of substituted styrenes but also to vinyl cyclopropanes and vinyl cyclobutane, affording the corresponding 1,5‐ and 1,6‐carboboration‐related products. Combined experimental and computational investigations reveal a mechanism that involves the Ziegler‐type carbometallation process. The synthetic utility is further highlighted by the facile one‐pot derivatization of the resulting benzylic boronates. Furthermore, a modified catalytic system offers an alternative to the anionic polymerization of styrene.
Document Type: article
File Description: electronic resource
Language: English
ISSN: 2198-3844
Relation: https://doaj.org/toc/2198-3844
DOI: 10.1002/advs.202511395
Access URL: https://doaj.org/article/4e1e74c7fa1f44a5890234f81f1a7bf4
Accession Number: edsdoj.4e1e74c7fa1f44a5890234f81f1a7bf4
Database: Directory of Open Access Journals
Description
Abstract:Abstract Carbometallation reaction represents a classic strategy for the bifunctionalization of unsaturated hydrocarbons, yet conventional implementations predominantly rely on either highly reactive organometallic reagents or transition metal catalysts. Notably, the direct employment of metalloid organoboron reagents for such addition processes remains elusive except when specific substrate combinations are employed. Herein, a base‐catalyzed carboboration reaction of aryl alkenes with bench‐stable benzylic boronates is reported. This anionic‐based strategy is not only applicable to the carboboration of substituted styrenes but also to vinyl cyclopropanes and vinyl cyclobutane, affording the corresponding 1,5‐ and 1,6‐carboboration‐related products. Combined experimental and computational investigations reveal a mechanism that involves the Ziegler‐type carbometallation process. The synthetic utility is further highlighted by the facile one‐pot derivatization of the resulting benzylic boronates. Furthermore, a modified catalytic system offers an alternative to the anionic polymerization of styrene.
ISSN:21983844
DOI:10.1002/advs.202511395