Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Guangzhu Wang; Xinyi Liang; Lili Chen; Qian Gao; Jian Guo Wang; Panke Zhang; Qian Peng; Senmiao Xu

doi:10.1002/anie.201902464

Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Guangzhu Wang, Xinyi Liang, Lili Chen, Qian Gao, Jian Guo Wang, Panke Zhang, Qian Peng, Senmiao Xu

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

33 Scopus citations

Abstract

The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected Ir^III/Ir^V cycle.

Original language	English
Pages (from-to)	8187-8191
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	24
DOIs	https://doi.org/10.1002/anie.201902464
State	Published - 11 Jun 2019
Externally published	Yes

Keywords

alkenes
alkyl boronic acids
hydroboration
iridium
synthetic methods

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10.1002/anie.201902464

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title = "Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes",

abstract = "The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle.",

keywords = "alkenes, alkyl boronic acids, hydroboration, iridium, synthetic methods",

author = "Guangzhu Wang and Xinyi Liang and Lili Chen and Qian Gao and Wang, \{Jian Guo\} and Panke Zhang and Qian Peng and Senmiao Xu",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/anie.201902464",

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T1 - Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

AU - Wang, Guangzhu

AU - Liang, Xinyi

AU - Chen, Lili

AU - Gao, Qian

AU - Wang, Jian Guo

AU - Zhang, Panke

AU - Peng, Qian

AU - Xu, Senmiao

PY - 2019/6/11

Y1 - 2019/6/11

N2 - The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle.

AB - The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle.

KW - alkenes

KW - alkyl boronic acids

KW - hydroboration

KW - iridium

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/85065915323

U2 - 10.1002/anie.201902464

DO - 10.1002/anie.201902464

M3 - 文章

C2 - 30990948

AN - SCOPUS:85065915323

SN - 1433-7851

VL - 58

SP - 8187

EP - 8191

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 24

ER -

Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

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Keywords

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