Iridium-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclobutanes

Xiang Chen; Lili Chen; Hongliang Zhao; Qian Gao; Zhenlu Shen; Senmiao Xu

doi:10.1002/cjoc.202000240

Iridium-Catalyzed Enantioselective C(sp³)–H Borylation of Cyclobutanes

Xiang Chen
, Lili Chen
, Hongliang Zhao
, Qian Gao
, Zhenlu Shen
, Senmiao Xu^*

^*Corresponding author for this work

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

56 Scopus citations

Abstract

We herein report the first example of iridium-catalyzed enantioselective C(sp³)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp³)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.

Original language	English
Pages (from-to)	1533-1537
Number of pages	5
Journal	Chinese Journal of Chemistry
Volume	38
Issue number	12
DOIs	https://doi.org/10.1002/cjoc.202000240
State	Published - Dec 2020
Externally published	Yes

Keywords

Asymmetric catalysis
Cyclobutane
C—H Borylation
Iridium
Organoboron

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10.1002/cjoc.202000240

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title = "Iridium-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclobutanes",

abstract = "We herein report the first example of iridium-catalyzed enantioselective C(sp3)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp3)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.",

keywords = "Asymmetric catalysis, Cyclobutane, C—H Borylation, Iridium, Organoboron",

author = "Xiang Chen and Lili Chen and Hongliang Zhao and Qian Gao and Zhenlu Shen and Senmiao Xu",

note = "Publisher Copyright: {\textcopyright} 2020 SIOC, CAS, Shanghai and Wiley-VCH GmbH",

year = "2020",

month = dec,

doi = "10.1002/cjoc.202000240",

language = "英语",

volume = "38",

pages = "1533--1537",

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T1 - Iridium-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclobutanes

AU - Chen, Xiang

AU - Chen, Lili

AU - Zhao, Hongliang

AU - Gao, Qian

AU - Shen, Zhenlu

AU - Xu, Senmiao

PY - 2020/12

Y1 - 2020/12

N2 - We herein report the first example of iridium-catalyzed enantioselective C(sp3)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp3)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.

AB - We herein report the first example of iridium-catalyzed enantioselective C(sp3)–H borylation of cyclobutanes using benzoxazoline as the directing group. The combination of a chiral bidentate boryl ligand and an iridium precursor has found to effectively catalyze C(sp3)–H borylation to afford a variety of cyclobutylboronates with good to excellent enantioselectivities. We also demonstrate the synthetic utility of the current method by converting the stereogenic C—B bond to other functionalities.

KW - Asymmetric catalysis

KW - Cyclobutane

KW - C—H Borylation

KW - Iridium

KW - Organoboron

UR - https://www.scopus.com/pages/publications/85090300311

U2 - 10.1002/cjoc.202000240

DO - 10.1002/cjoc.202000240

M3 - 文章

AN - SCOPUS:85090300311

SN - 1001-604X

VL - 38

SP - 1533

EP - 1537

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 12

ER -

Iridium-Catalyzed Enantioselective C(sp³)–H Borylation of Cyclobutanes

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