Please use this identifier to cite or link to this item:
http://hdl.handle.net/10397/96179
Title: | Pd(II)-catalyzed direct ortho-C-H acylation of aromatic ketones by oxidative decarboxylation of α-oxocarboxylic acids | Authors: | Lee, PY Liang, P Yu, WY |
Issue Date: | 21-Apr-2017 | Source: | Organic letters, 21 Apr. 2017, v. 19, no. 8, p. 2082-2085 | Abstract: | A Pd-catalyzed decarboxylative acylation of aromatic ketones with α-oxocarboxylic acids was developed, and 1,2-diacylbenzenes were formed in up to 90% yield with excellent ortho-selectivity. This work demonstrates the first successful attempt to direct C-H acylation of aromatic ketones without the need for prederivatization to imines. The acylation reaction was inhibited by radical scavengers such as TEMPO, and 2,2,6,6-tetramethylpiperidin-1-yl benzoate, the adduct of TEMPO and a benzoyl radical, has been isolated and characterized. This finding is compatible with the intermediacy of acyl radicals. A mechanism involving the reaction of the palladacyclic complexes of aryl ketones with acyl radicals is proposed. | Publisher: | American Chemical Society | Journal: | Organic letters | ISSN: | 1523-7060 | EISSN: | 1523-7052 | DOI: | 10.1021/acs.orglett.7b00677 | Rights: | © 2017 American Chemical Society This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b00677. |
Appears in Collections: | Journal/Magazine Article |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
PdII-Catalyzed_Direct_Ortho-C-H.pdf | Pre-Published version | 474.58 kB | Adobe PDF | View/Open |
Page views
65
Last Week
0
0
Last month
Citations as of Sep 22, 2024
Downloads
72
Citations as of Sep 22, 2024
SCOPUSTM
Citations
49
Citations as of Sep 26, 2024
WEB OF SCIENCETM
Citations
47
Citations as of Sep 26, 2024
Google ScholarTM
Check
Altmetric
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.