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Synlett 2012(3): 375-380  
DOI: 10.1055/s-0031-1290203
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© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Mediated Highly Regio- and Stereoselective Intermolecular β-Arylation on Allylic Alcohols: Synthesis of Functionalized Allylic Alcohols

J. Krishna, A. Gopi Krishna Reddy, B. Venkat Ramulu, L. Mahendar, G. Satyanarayana*
Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram 502 205, Medak District, Andhra Pradesh, India
Fax: +91(40)23016032; e-Mail: gvsatya@iith.ac.in;
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Publication History

Received 25 October 2011
Publication Date:
26 January 2012 (online)

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Abstract

An efficient and highly regio- and stereoselctive Pd-catalyzed β-arylation method for the formation of β-aryl allylic alcohols, employing aryl iodides, 1-bromo-2-iodobenzenes, and 2-bromobezaldehydes as coupling partners, is presented. The β-aryl allylic alcohols formed in this Pd-catalyzed transformation is unexpected under conventional Jeffery conditions without the assistance of silver salt. It is proposed that the reaction is substrate controlled, and the selective formation of the product depends on the size or nature of the substituent at the ortho position on the aromatic ring of the allylic alcohol part.

Key words

Pd catalysis - β-arylation - Mizoroki-Heck - allylic alcohols - β-carbonyls

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