Preparation of 2-aryl derivatives of tanshinone I through a palladium-catalyzed C-sp2-H activation/arylation approach

A facile and efficient synthetic approach under the catalyst system of Pd(OAc)(2)/KOAc/TBAB/DMF was developed allowing for rapid preparation of 2-arylation derivatives of the natural product tanshinone I. This approach was featured by palladium-catalyzed C-C coupling through direct C-sp2-H activatio...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 21; pp. 2799 - 2802
Main Authors Jiao, Mingkun, Ding, Chunyong, Zhang, Ao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 20.05.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ARYLATIONS
FURAN
C-H activation
INHIBITION
SALVIA-MILTIORRHIZA BUNGE
Direct arylation
Palladium
Anticancer
C-H FUNCTIONALIZATION
CRYPTOTANSHINONE
Tanshinone I
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Summary:A facile and efficient synthetic approach under the catalyst system of Pd(OAc)(2)/KOAc/TBAB/DMF was developed allowing for rapid preparation of 2-arylation derivatives of the natural product tanshinone I. This approach was featured by palladium-catalyzed C-C coupling through direct C-sp2-H activation at the a-position of the furan ring of tanshinone I. Compared to the literature procedures, our protocol exhibited better atom-economy and much improved yields. (C) 2015 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2015.04.040