Copper- and cobalt-catalyzed direct coupling of sp3 α-carbon of alcohols with alkenes and hydroperoxides

Jun Kee Cheng; Teck Peng Loh

doi:10.1021/ja510635k

Copper- and cobalt-catalyzed direct coupling of sp³ α-carbon of alcohols with alkenes and hydroperoxides

Jun Kee Cheng, Teck Peng Loh^*

^*Corresponding author for this work

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

190 Citations (Scopus)

Abstract

A zerovalent copper- and cobalt-catalyzed direct coupling of the sp³ α-carbon of alcohols with alkenes and hydroperoxides was developed in which the hydroperoxides acted as radical initiator and then coupling partner. 1,3-Enynes and vinylarenes underwent alkylation-peroxidation to give β-peroxy alcohols and β-hydroxyketones correspondingly with excellent functional group tolerance. The resulting β-peroxy alcohols could be further transformed into β-hydroxyynones and propargylic 1,3-diols.

Original language	English
Pages (from-to)	42-45
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	1
DOIs	https://doi.org/10.1021/ja510635k
Publication status	Published - Jan 14 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja510635k

Cite this

@article{39c73d6cabbb4216a38aef511b09943e,

title = "Copper- and cobalt-catalyzed direct coupling of sp3 α-carbon of alcohols with alkenes and hydroperoxides",

abstract = "A zerovalent copper- and cobalt-catalyzed direct coupling of the sp3 α-carbon of alcohols with alkenes and hydroperoxides was developed in which the hydroperoxides acted as radical initiator and then coupling partner. 1,3-Enynes and vinylarenes underwent alkylation-peroxidation to give β-peroxy alcohols and β-hydroxyketones correspondingly with excellent functional group tolerance. The resulting β-peroxy alcohols could be further transformed into β-hydroxyynones and propargylic 1,3-diols.",

author = "Cheng, \{Jun Kee\} and Loh, \{Teck Peng\}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2015",

month = jan,

day = "14",

doi = "10.1021/ja510635k",

language = "English",

volume = "137",

pages = "42--45",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Copper- and cobalt-catalyzed direct coupling of sp3 α-carbon of alcohols with alkenes and hydroperoxides

AU - Cheng, Jun Kee

AU - Loh, Teck Peng

PY - 2015/1/14

Y1 - 2015/1/14

N2 - A zerovalent copper- and cobalt-catalyzed direct coupling of the sp3 α-carbon of alcohols with alkenes and hydroperoxides was developed in which the hydroperoxides acted as radical initiator and then coupling partner. 1,3-Enynes and vinylarenes underwent alkylation-peroxidation to give β-peroxy alcohols and β-hydroxyketones correspondingly with excellent functional group tolerance. The resulting β-peroxy alcohols could be further transformed into β-hydroxyynones and propargylic 1,3-diols.

AB - A zerovalent copper- and cobalt-catalyzed direct coupling of the sp3 α-carbon of alcohols with alkenes and hydroperoxides was developed in which the hydroperoxides acted as radical initiator and then coupling partner. 1,3-Enynes and vinylarenes underwent alkylation-peroxidation to give β-peroxy alcohols and β-hydroxyketones correspondingly with excellent functional group tolerance. The resulting β-peroxy alcohols could be further transformed into β-hydroxyynones and propargylic 1,3-diols.

UR - http://www.scopus.com/inward/record.url?scp=84921030510&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84921030510&partnerID=8YFLogxK

U2 - 10.1021/ja510635k

DO - 10.1021/ja510635k

M3 - Article

AN - SCOPUS:84921030510

SN - 0002-7863

VL - 137

SP - 42

EP - 45

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 1

ER -