PMA-Silica Gel Catalyzed Propargylation of Aromatic Compounds with Arylpropargyl Alcohols under Solvent-Free Conditions [1]

Abstract

PMA-silica gel has been utilized to catalyze efficiently the propargylation of aromatic compounds with arylpropargyl alcohols in the absence of solvent under environmentally benign conditions.

Key words

propargylation - nucleophilic substitution - Nicholas reaction­ - Friedel-Crafts alkylation

1

IICT Communication No. 061220

References

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1

IICT Communication No. 061220

15

Propargyl alcohols were prepared according to the earlier known procedures from monosubstituted acetylenes and corresponding aldehydes using EtMgBr.

16

The compound 1a (Table [4] , entry 1) was studied for three runs (90%, 88%, and 85% yields respectively).

17

All the reactions were run with 1 mol% PMA-silica gel at r.t. in MeCN unless specified.

18

Substitution was present at the para position (least hindered site with high electron density) and was confirmed by ¹H NMR spectroscopy. No other products were formed in this reaction.