Three-component cascade carbopalladation/Heck cyclization/borylation: facile access to boryl-functionalized indenes

A mild Pd-catalyzed three-component cascade cyclization functionalization of o -iodostyrenes, internal alkynes and boron reagents is presented. The transformation is driven by a controlled reaction sequence of intermolecular carbopalladation, intramolecular Heck-type cyclization, and a borylation pr...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-07, Vol.6 (62), p.875-878
Main Authors: Sun, Fei, Zheng, Yiyi, Wu, Mingxia, Ji, Hongsen, Jiang, Zhongyao, Liu, Chenglin, Wu, Xin-Xing
Format: Article
Language:English
Subjects:
Alkynes
Boron
Indene
Reagents
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Summary:A mild Pd-catalyzed three-component cascade cyclization functionalization of o -iodostyrenes, internal alkynes and boron reagents is presented. The transformation is driven by a controlled reaction sequence of intermolecular carbopalladation, intramolecular Heck-type cyclization, and a borylation process to give versatile boryl-functionalized indene skeletons in a selective fashion. Significantly, (Bpin) 2 , (Bneop) 2 and CH 2 (Bpin) 2 as boron sources are all tolerated. Additionally, the synthetic utility of this approach is demonstrated by gram-scale synthesis and synthetic transformations. A mild Pd-catalyzed three-component cascade cyclization functionalization of o -iodostyrenes, internal alkynes and boron reagents for versatile boryl-functionalized indenes is presented.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc02591a