Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

3-2003

Journal or Book Title

Organometallics

Volume

22

Issue

7

First Page

1468

Last Page

1474

DOI

10.1021/om020904o

Abstract

Iron(II) meso-tetraphenylporphyrin is an efficient catalyst for the selective olefination of a variety of aromatic and aliphatic aldehydes with use of ethyl diazoacetate in the presence of triphenylphosphine. These reactions gave olefin products in excellent yields (>85%) with high selectivity for the E-isomer (>90%). For the olefination of ketones, the reactions were generally slow and the selectivities were low compared with those observed with aldehydes. Iron(III)meso-tetraphenylporphyrin chloride, reduced in situ, could be used as an olefination precatalyst to produce similar yields and selectivities. The olefination mechanism was investigated and the likely pathways are discussed.

Comments

Reprinted (adapted) with permission from Organometallics 22 (2003): 1468, doi:10.1021/om020904o. Copyright 2003 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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