Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate

Haruki Mizoguchi; Masaya Seriu; Akira Sakakura

doi:10.1039/d0cc07134j

Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate

Haruki Mizoguchi, Masaya Seriu, Akira Sakakura

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Abstract

A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. This journal is

Original language	English
Pages (from-to)	15545-15548
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	99
DOIs	https://doi.org/10.1039/d0cc07134j
Publication status	Published - Dec 25 2020

ASJC Scopus subject areas

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/d0cc07134j

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title = "Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate",

abstract = "A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. This journal is ",

author = "Haruki Mizoguchi and Masaya Seriu and Akira Sakakura",

note = "Funding Information: This work was supported by a Grant-in-Aid from JSPS KAKENHI (19K21128, 20K15282), and a grant from the Uehara Memorial Foundation. The authors gratefully thank the Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University, for the NMR and HRMS measurements. The authors are grateful to Dr Hiromi Ota at the Division of Instrumental Analysis for the X-ray single-crystal structural analyses. The authors are grateful to Dr Koichi Mitsudo (Okayama University) for useful discussions regarding DFT calculations. Publisher Copyright: {\textcopyright} 2020 The Royal Society of Chemistry.",

year = "2020",

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doi = "10.1039/d0cc07134j",

language = "English",

volume = "56",

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journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate

AU - Mizoguchi, Haruki

AU - Seriu, Masaya

AU - Sakakura, Akira

N1 - Funding Information: This work was supported by a Grant-in-Aid from JSPS KAKENHI (19K21128, 20K15282), and a grant from the Uehara Memorial Foundation. The authors gratefully thank the Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University, for the NMR and HRMS measurements. The authors are grateful to Dr Hiromi Ota at the Division of Instrumental Analysis for the X-ray single-crystal structural analyses. The authors are grateful to Dr Koichi Mitsudo (Okayama University) for useful discussions regarding DFT calculations. Publisher Copyright: © 2020 The Royal Society of Chemistry.

PY - 2020/12/25

Y1 - 2020/12/25

N2 - A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. This journal is

AB - A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. This journal is

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Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate

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