Competing Dehalogenation versus Borylation of Aryl Iodides and Bromides under Transition-Metal-Free Basic Conditions

In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation...

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Published inJournal of organic chemistry Vol. 84; no. 17; pp. 10805 - 10813
Main Authors Niu, Yi-Jie, Sui, Guo-Hui, Zheng, Hong-Xing, Shan, Xiang-Huan, Tie, Lin, Fu, Jia-Le, Qu, Jian-Ping, Kang, Yan-Biao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
CROSS-COUPLING REACTIONS
ELECTRON
ACTIVATION
REDUCTION
SECONDARY
ORGANIC HALIDES
COPPER-CATALYZED BORYLATION
ALKOXY DIBORON REAGENTS
ALKYL-HALIDES
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Summary:In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as a hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the t BuOK/1,10-Phen-triggered radical nature of both competitive reactions has been revealed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01350