The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

Prakash Basnet; Surendra Thapa; Diane A. Dickie; Ramesh Giri

doi:10.1039/c6cc05114f

The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

Prakash Basnet, Surendra Thapa, Diane A. Dickie, Ramesh Giri

Chemistry

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28 Scopus citations

Abstract

We report the first example of Cu^I-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a Cu^I-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.

Original language	English (US)
Pages (from-to)	11072-11075
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	74
DOIs	https://doi.org/10.1039/c6cc05114f
State	Published - Sep 25 2016

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c6cc05114f

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title = "The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation",

abstract = "We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.",

author = "Prakash Basnet and Surendra Thapa and Dickie, {Diane A.} and Ramesh Giri",

note = "Funding Information: We thank the University of New Mexico (UNM) and the National Science Foundation (NSF CHE-1554299) for financial support, and upgrades to the NMR (NSF grants CHE08-40523 and CHE09-46690) and MS Facilities. The Bruker X-ray diffractometer was purchased via an NSF CRIF:MU award to UNM (CHE04-43580).",

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doi = "10.1039/c6cc05114f",

language = "English (US)",

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The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation. / Basnet, Prakash; Thapa, Surendra; Dickie, Diane A. et al.
In: Chemical Communications, Vol. 52, No. 74, 25.09.2016, p. 11072-11075.

Research output: Contribution to journal › Article › peer-review

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AU - Basnet, Prakash

AU - Thapa, Surendra

AU - Dickie, Diane A.

AU - Giri, Ramesh

N1 - Funding Information: We thank the University of New Mexico (UNM) and the National Science Foundation (NSF CHE-1554299) for financial support, and upgrades to the NMR (NSF grants CHE08-40523 and CHE09-46690) and MS Facilities. The Bruker X-ray diffractometer was purchased via an NSF CRIF:MU award to UNM (CHE04-43580).

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Y1 - 2016/9/25

N2 - We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.

AB - We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.

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The copper-catalysed Suzuki-Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

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