Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

Takahide Fukuyama; Takanobu Bando; Ilhyong Ryu

doi:10.1055/s-0037-1609964

Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

Takahide Fukuyama, Takanobu Bando, Ilhyong Ryu^*

^*Corresponding author for this work

Department of Applied Chemistry

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

15 Scopus citations

Abstract

A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

Original language	English
Article number	ss-2018-c0146-st
Pages (from-to)	3015-3021
Number of pages	7
Journal	Synthesis (Germany)
Volume	50
Issue number	15
DOIs	https://doi.org/10.1055/s-0037-1609964
State	Published - Aug 2018

Keywords

carbonylation
electron transfer
lactams
lactones
metal-free
radical reactions

Access to Document

10.1055/s-0037-1609964

Cite this

@article{5c33aa3736344e7882f276581d8f008b,

title = "Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams",

abstract = "A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.",

keywords = "carbonylation, electron transfer, lactams, lactones, metal-free, radical reactions",

author = "Takahide Fukuyama and Takanobu Bando and Ilhyong Ryu",

year = "2018",

month = aug,

doi = "10.1055/s-0037-1609964",

language = "English",

volume = "50",

pages = "3015--3021",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "15",

}

TY - JOUR

T1 - Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

AU - Fukuyama, Takahide

AU - Bando, Takanobu

AU - Ryu, Ilhyong

PY - 2018/8

Y1 - 2018/8

N2 - A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

AB - A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

KW - carbonylation

KW - electron transfer

KW - lactams

KW - lactones

KW - metal-free

KW - radical reactions

UR - http://www.scopus.com/inward/record.url?scp=85048010897&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1609964

DO - 10.1055/s-0037-1609964

M3 - Article

AN - SCOPUS:85048010897

SN - 0039-7881

VL - 50

SP - 3015

EP - 3021

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 15

M1 - ss-2018-c0146-st

ER -

Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this