Chromium-Catalyzed Selective Dimerization/Hydroboration of Allenes to Access Boryl-Functionalized Skipped (E,Z)-Dienes

Yinsong Zhao; Shaozhong Ge

doi:10.1002/anie.202012344

Chromium-Catalyzed Selective Dimerization/Hydroboration of Allenes to Access Boryl-Functionalized Skipped (E,Z)-Dienes

Yinsong Zhao
, Shaozhong Ge^*

^*Corresponding author for this work

National University of Singapore

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

30 Scopus citations

Abstract

A chromium-catalyzed dimerization/hydroboration of allenes is developed to access synthetically versatile boryl-functionalized skipped dienes with a catalyst generated in situ from CrCl₂ and a pyridine-2,6-diimine ligand ^mesPDI. A variety of allenes reacted with pinacolborane (HBpin) to afford the corresponding boryl-functionalized (E,Z)-1,4-dienes in high yields and with excellent selectivity. Electron paramagnetic resonance (EPR) spectroscopic studies suggest that this chromium-catalyzed reaction probably proceeds through a chromium(I) hydride intermediate.

Original language	English
Pages (from-to)	2149-2154
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	4
DOIs	https://doi.org/10.1002/anie.202012344
State	Published - 25 Jan 2021
Externally published	Yes

Keywords

allenes
chromium
dimerization
homogeneous catalysis
hydroboration

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10.1002/anie.202012344

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title = "Chromium-Catalyzed Selective Dimerization/Hydroboration of Allenes to Access Boryl-Functionalized Skipped (E,Z)-Dienes",

abstract = "A chromium-catalyzed dimerization/hydroboration of allenes is developed to access synthetically versatile boryl-functionalized skipped dienes with a catalyst generated in situ from CrCl2 and a pyridine-2,6-diimine ligand mesPDI. A variety of allenes reacted with pinacolborane (HBpin) to afford the corresponding boryl-functionalized (E,Z)-1,4-dienes in high yields and with excellent selectivity. Electron paramagnetic resonance (EPR) spectroscopic studies suggest that this chromium-catalyzed reaction probably proceeds through a chromium(I) hydride intermediate.",

keywords = "allenes, chromium, dimerization, homogeneous catalysis, hydroboration",

author = "Yinsong Zhao and Shaozhong Ge",

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AU - Zhao, Yinsong

AU - Ge, Shaozhong

PY - 2021/1/25

Y1 - 2021/1/25

N2 - A chromium-catalyzed dimerization/hydroboration of allenes is developed to access synthetically versatile boryl-functionalized skipped dienes with a catalyst generated in situ from CrCl2 and a pyridine-2,6-diimine ligand mesPDI. A variety of allenes reacted with pinacolborane (HBpin) to afford the corresponding boryl-functionalized (E,Z)-1,4-dienes in high yields and with excellent selectivity. Electron paramagnetic resonance (EPR) spectroscopic studies suggest that this chromium-catalyzed reaction probably proceeds through a chromium(I) hydride intermediate.

AB - A chromium-catalyzed dimerization/hydroboration of allenes is developed to access synthetically versatile boryl-functionalized skipped dienes with a catalyst generated in situ from CrCl2 and a pyridine-2,6-diimine ligand mesPDI. A variety of allenes reacted with pinacolborane (HBpin) to afford the corresponding boryl-functionalized (E,Z)-1,4-dienes in high yields and with excellent selectivity. Electron paramagnetic resonance (EPR) spectroscopic studies suggest that this chromium-catalyzed reaction probably proceeds through a chromium(I) hydride intermediate.

KW - allenes

KW - chromium

KW - dimerization

KW - homogeneous catalysis

KW - hydroboration

UR - https://www.scopus.com/pages/publications/85096657652

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DO - 10.1002/anie.202012344

M3 - 文章

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AN - SCOPUS:85096657652

SN - 1433-7851

VL - 60

SP - 2149

EP - 2154

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 4

ER -

Chromium-Catalyzed Selective Dimerization/Hydroboration of Allenes to Access Boryl-Functionalized Skipped (E,Z)-Dienes

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