New and effective aerobic oxygenation of olefins catalyzed by transition-metal complexes

Tohru Yamada, Toshihiro Takai, Teruaki Mukaiyama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

New and effective aerobic oxygenation reactions of olefins catalyzed by transition-metal complexes are described. (1) By the combined use of an atmospheric pressure of molecular oxygen and secondary alcohols, various kinds of olefins are converted into the corresponding alcohols in good to high yields catalyzed by a cobalt (II) complex. (2) Effective epoxidation of a wide variety of olefins involving styrenes and α,β-unsaturated carboxamide are achieved by the combination use of aldehyde and molecular oxygen catalyzed by nickel (II), iron (III), or oxovanadium (IV) complexes under mild reaction conditions. (3) Enantioselective aerobic epoxidations of unfunctionalized olefins are demonstrated by using optically active manganese (III) complexes as catalysts. (4) In the presence of acetal of aldehyde, cobalt (II) complex catalyzed aerobic epoxidation of olefins proceeds in high yield under neutral and mild conditions.

Original languageEnglish
Pages (from-to)995-1004
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume51
Issue number11
Publication statusPublished - 1993 Nov
Externally publishedYes

Fingerprint

Oxygenation
Coordination Complexes
Alkenes
Transition metals
Epoxidation
Molecular oxygen
Cobalt
Aldehydes
Styrenes
Alcohols
Acetals
Manganese
Nickel
Atmospheric pressure
Iron
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

New and effective aerobic oxygenation of olefins catalyzed by transition-metal complexes. / Yamada, Tohru; Takai, Toshihiro; Mukaiyama, Teruaki.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 51, No. 11, 11.1993, p. 995-1004.

Research output: Contribution to journalArticle

@article{06b3956298fe494e926a4985e7a867e7,
title = "New and effective aerobic oxygenation of olefins catalyzed by transition-metal complexes",
abstract = "New and effective aerobic oxygenation reactions of olefins catalyzed by transition-metal complexes are described. (1) By the combined use of an atmospheric pressure of molecular oxygen and secondary alcohols, various kinds of olefins are converted into the corresponding alcohols in good to high yields catalyzed by a cobalt (II) complex. (2) Effective epoxidation of a wide variety of olefins involving styrenes and α,β-unsaturated carboxamide are achieved by the combination use of aldehyde and molecular oxygen catalyzed by nickel (II), iron (III), or oxovanadium (IV) complexes under mild reaction conditions. (3) Enantioselective aerobic epoxidations of unfunctionalized olefins are demonstrated by using optically active manganese (III) complexes as catalysts. (4) In the presence of acetal of aldehyde, cobalt (II) complex catalyzed aerobic epoxidation of olefins proceeds in high yield under neutral and mild conditions.",
author = "Tohru Yamada and Toshihiro Takai and Teruaki Mukaiyama",
year = "1993",
month = "11",
language = "English",
volume = "51",
pages = "995--1004",
journal = "Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry",
issn = "0037-9980",
publisher = "Society of Synthetic Organic Chemistry",
number = "11",

}

TY - JOUR

T1 - New and effective aerobic oxygenation of olefins catalyzed by transition-metal complexes

AU - Yamada, Tohru

AU - Takai, Toshihiro

AU - Mukaiyama, Teruaki

PY - 1993/11

Y1 - 1993/11

N2 - New and effective aerobic oxygenation reactions of olefins catalyzed by transition-metal complexes are described. (1) By the combined use of an atmospheric pressure of molecular oxygen and secondary alcohols, various kinds of olefins are converted into the corresponding alcohols in good to high yields catalyzed by a cobalt (II) complex. (2) Effective epoxidation of a wide variety of olefins involving styrenes and α,β-unsaturated carboxamide are achieved by the combination use of aldehyde and molecular oxygen catalyzed by nickel (II), iron (III), or oxovanadium (IV) complexes under mild reaction conditions. (3) Enantioselective aerobic epoxidations of unfunctionalized olefins are demonstrated by using optically active manganese (III) complexes as catalysts. (4) In the presence of acetal of aldehyde, cobalt (II) complex catalyzed aerobic epoxidation of olefins proceeds in high yield under neutral and mild conditions.

AB - New and effective aerobic oxygenation reactions of olefins catalyzed by transition-metal complexes are described. (1) By the combined use of an atmospheric pressure of molecular oxygen and secondary alcohols, various kinds of olefins are converted into the corresponding alcohols in good to high yields catalyzed by a cobalt (II) complex. (2) Effective epoxidation of a wide variety of olefins involving styrenes and α,β-unsaturated carboxamide are achieved by the combination use of aldehyde and molecular oxygen catalyzed by nickel (II), iron (III), or oxovanadium (IV) complexes under mild reaction conditions. (3) Enantioselective aerobic epoxidations of unfunctionalized olefins are demonstrated by using optically active manganese (III) complexes as catalysts. (4) In the presence of acetal of aldehyde, cobalt (II) complex catalyzed aerobic epoxidation of olefins proceeds in high yield under neutral and mild conditions.

UR - http://www.scopus.com/inward/record.url?scp=0027699329&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027699329&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0027699329

VL - 51

SP - 995

EP - 1004

JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

SN - 0037-9980

IS - 11

ER -