Earth-Abundant Metal Catalysis Enabled by Counterion Activation

Riaz Agahi; Amy J. Challinor; Neil B. Carter; Stephen P. Thomas

doi:10.1021/acs.orglett.8b03986

Earth-Abundant Metal Catalysis Enabled by Counterion Activation

Riaz Agahi, Amy J. Challinor, Neil B. Carter, Stephen P. Thomas

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

Abstract

A pre-catalyst activation strategy has been developed for Earth-abundant metal catalysis enabled by counterion dissociation and demonstrated through alkene hydroboration. Commercially available iron- and cobalt tetrafluoroborate salts were found to catalyze the hydroboration of aryl- and alkyl alkenes with good functional group tolerance (Fe, 12 substrates; Co, 13 substrates) with 3 structurally distinct ligands. Key to this endogenous activation was counterion dissociation to generate fluoride which indirectly activates the pre-catalyst by reaction with pinacol borane.

Original language	English
Journal	Organic letters
Early online date	4 Feb 2019
DOIs	https://doi.org/10.1021/acs.orglett.8b03986
Publication status	E-pub ahead of print - 4 Feb 2019

Access to Document

10.1021/acs.orglett.8b03986

20190206 Thomas Earth-abundant Metal Catalysis Enabled by Counterion Activation submittedAccepted author manuscript, 1.23 MBLicence: Creative Commons: Attribution Non-Commercial (CC-BY-NC)

http://pubs.acs.org/doi/10.1021/acs.orglett.8b03986

Cite this

@article{dfc79f293aab4a1ca5e28ca5a6914ddc,

title = "Earth-Abundant Metal Catalysis Enabled by Counterion Activation",

abstract = "A pre-catalyst activation strategy has been developed for Earth-abundant metal catalysis enabled by counterion dissociation and demonstrated through alkene hydroboration. Commercially available iron- and cobalt tetrafluoroborate salts were found to catalyze the hydroboration of aryl- and alkyl alkenes with good functional group tolerance (Fe, 12 substrates; Co, 13 substrates) with 3 structurally distinct ligands. Key to this endogenous activation was counterion dissociation to generate fluoride which indirectly activates the pre-catalyst by reaction with pinacol borane.",

author = "Riaz Agahi and Challinor, \{Amy J.\} and Carter, \{Neil B.\} and Thomas, \{Stephen P.\}",

year = "2019",

month = feb,

day = "4",

doi = "10.1021/acs.orglett.8b03986",

language = "English",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Earth-Abundant Metal Catalysis Enabled by Counterion Activation

AU - Agahi, Riaz

AU - Challinor, Amy J.

AU - Carter, Neil B.

AU - Thomas, Stephen P.

PY - 2019/2/4

Y1 - 2019/2/4

N2 - A pre-catalyst activation strategy has been developed for Earth-abundant metal catalysis enabled by counterion dissociation and demonstrated through alkene hydroboration. Commercially available iron- and cobalt tetrafluoroborate salts were found to catalyze the hydroboration of aryl- and alkyl alkenes with good functional group tolerance (Fe, 12 substrates; Co, 13 substrates) with 3 structurally distinct ligands. Key to this endogenous activation was counterion dissociation to generate fluoride which indirectly activates the pre-catalyst by reaction with pinacol borane.

AB - A pre-catalyst activation strategy has been developed for Earth-abundant metal catalysis enabled by counterion dissociation and demonstrated through alkene hydroboration. Commercially available iron- and cobalt tetrafluoroborate salts were found to catalyze the hydroboration of aryl- and alkyl alkenes with good functional group tolerance (Fe, 12 substrates; Co, 13 substrates) with 3 structurally distinct ligands. Key to this endogenous activation was counterion dissociation to generate fluoride which indirectly activates the pre-catalyst by reaction with pinacol borane.

U2 - 10.1021/acs.orglett.8b03986

DO - 10.1021/acs.orglett.8b03986

M3 - Article

SN - 1523-7060

JO - Organic letters

JF - Organic letters

ER -

Earth-Abundant Metal Catalysis Enabled by Counterion Activation

Abstract

Access to Document

Fingerprint

Cite this