Ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols

Xiaoxiang Zhang; Wan Teng Teo; Philip Wai Hong Chan

doi:10.1021/ol901981s

Ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols

Org Lett. 2009 Nov 5;11(21):4990-3. doi: 10.1021/ol901981s.

Authors

Xiaoxiang Zhang¹, Wan Teng Teo, Philip Wai Hong Chan

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore.

PMID: 19863152
DOI: 10.1021/ol901981s

Abstract

A method to prepare indenols efficiently by ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols is described. The reaction was accomplished in moderate to excellent yields and regioselectivity under mild conditions and offers a straightforward and convenient one step synthetic route to bioactive indenols and its derivatives.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemical synthesis*
Alcohols / chemistry
Alkynes / chemistry*
Catalysis
Cyclization
Indenes / chemical synthesis*
Indenes / chemistry
Mesylates / chemistry
Molecular Structure
Phenols / chemistry
Propanolamines / chemical synthesis*
Propanolamines / chemistry
Propanols / chemistry*
Ytterbium / chemistry*

Substances

Alcohols
Alkynes
Indenes
Mesylates
Phenols
Propanolamines
Propanols
indenolol
propargyl alcohol
Ytterbium