Synthesis of DBpin using Earth-abundant metal catalysis

Andrew W.m. Cummins; Shuyang Li; Dominic R. Willcox; Tommi Muilu; Jamie H. Docherty; Stephen P. Thomas

doi:10.1016/j.tet.2020.131084

Synthesis of DBpin using Earth-abundant metal catalysis

Andrew W.m. Cummins, Shuyang Li, Dominic R. Willcox, Tommi Muilu, Jamie H. Docherty, Stephen P. Thomas

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

Abstract

The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.

Original language	English
Pages (from-to)	131084
Journal	Tetrahedron
Early online date	29 Feb 2020
DOIs	https://doi.org/10.1016/j.tet.2020.131084
Publication status	E-pub ahead of print - 29 Feb 2020

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title = "Synthesis of DBpin using Earth-abundant metal catalysis",

abstract = "The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.",

author = "Cummins, {Andrew W.m.} and Shuyang Li and Willcox, {Dominic R.} and Tommi Muilu and Docherty, {Jamie H.} and Thomas, {Stephen P.}",

year = "2020",

month = feb,

day = "29",

doi = "10.1016/j.tet.2020.131084",

language = "English",

pages = "131084",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis of DBpin using Earth-abundant metal catalysis

AU - Cummins, Andrew W.m.

AU - Li, Shuyang

AU - Willcox, Dominic R.

AU - Muilu, Tommi

AU - Docherty, Jamie H.

AU - Thomas, Stephen P.

PY - 2020/2/29

Y1 - 2020/2/29

N2 - The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.

AB - The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.

U2 - 10.1016/j.tet.2020.131084

DO - 10.1016/j.tet.2020.131084

M3 - Article

SN - 0040-4020

SP - 131084

JO - Tetrahedron

JF - Tetrahedron

ER -

Synthesis of DBpin using Earth-abundant metal catalysis

Abstract

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