Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines: Synthesis and reactivity of α-oxygenated ketones

Alexander A. Andia; Matthew R. Miner; K. A. Woerpel

doi:10.1021/acs.orglett.5b01120

Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines: Synthesis and reactivity of α-oxygenated ketones

Alexander A. Andia, Matthew R. Miner, K. A. Woerpel

Chemistry

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

Abstract

The copper(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxyphthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided α-oxygenated ketones. The reaction proceeded under a balloon of O₂ at room temperature to furnish the dioxygenated products in 50-90% yield. These compounds, particularly the HOBt derivatives, can be further functionalized with phosphorus, nitrogen, and sulfur nucleophiles to give synthetically useful products.

Original language	English (US)
Pages (from-to)	2704-2707
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b01120
State	Published - Jun 5 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5b01120

Cite this

@article{19c8b7d286794152a0672718277a9f32,

title = "Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines: Synthesis and reactivity of α-oxygenated ketones",

abstract = "The copper(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxyphthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided α-oxygenated ketones. The reaction proceeded under a balloon of O2 at room temperature to furnish the dioxygenated products in 50-90% yield. These compounds, particularly the HOBt derivatives, can be further functionalized with phosphorus, nitrogen, and sulfur nucleophiles to give synthetically useful products.",

author = "Andia, {Alexander A.} and Miner, {Matthew R.} and Woerpel, {K. A.}",

year = "2015",

month = jun,

day = "5",

doi = "10.1021/acs.orglett.5b01120",

language = "English (US)",

volume = "17",

pages = "2704--2707",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines

T2 - Synthesis and reactivity of α-oxygenated ketones

AU - Andia, Alexander A.

AU - Miner, Matthew R.

AU - Woerpel, K. A.

PY - 2015/6/5

Y1 - 2015/6/5

N2 - The copper(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxyphthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided α-oxygenated ketones. The reaction proceeded under a balloon of O2 at room temperature to furnish the dioxygenated products in 50-90% yield. These compounds, particularly the HOBt derivatives, can be further functionalized with phosphorus, nitrogen, and sulfur nucleophiles to give synthetically useful products.

AB - The copper(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxyphthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided α-oxygenated ketones. The reaction proceeded under a balloon of O2 at room temperature to furnish the dioxygenated products in 50-90% yield. These compounds, particularly the HOBt derivatives, can be further functionalized with phosphorus, nitrogen, and sulfur nucleophiles to give synthetically useful products.

UR - http://www.scopus.com/inward/record.url?scp=84930940706&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84930940706&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b01120

DO - 10.1021/acs.orglett.5b01120

M3 - Article

AN - SCOPUS:84930940706

SN - 1523-7060

VL - 17

SP - 2704

EP - 2707

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines: Synthesis and reactivity of α-oxygenated ketones

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this