Bedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water

Anna Zernickel, weiyuan du, Seema Ghorpade, Dinesh Sawant, Arwa Makki, Nagaiyan Sekar, Jörg Eppinger

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 hours in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
Original languageEnglish (US)
Pages (from-to)1842-1851
Number of pages10
JournalThe Journal of Organic Chemistry
Volume83
Issue number4
DOIs
StatePublished - Jan 30 2018

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): FIC/2010/07
Acknowledgements: This work was supported by the King Abdullah University of Science and Technology (KAUST baseline funding and GCR grant FIC/2010/07). Authors are gratefully acknowledging support from King Abdullah University of Science and Technology (KAUST), Saudi Arabia.

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