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Synthesis 2012(1): 66-69  
DOI: 10.1055/s-0031-1289527
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© Georg Thieme Verlag Stuttgart ˙ New York

Nanoporous Gold-Catalyzed [4+2] Benzannulation between ortho-Alkynylbenzaldehydes and Alkynes

Naoki Asao*a, Menggenbateerb, Yohei Seyac, Yoshinori Yamamoto*a, Mingwei Chena, Wei Zhangd, Akihisa Inoued
a WPI Advanced Institute for Materials Research, Tohoku University, Sendai 980-8577, Japan
Fax: +81(22)2176165; e-Mail: asao@m.tohoku.ac.jp; e-Mail: yoshi@m.tohoku.ac.jp;
b Center for Integrated NanoTechnology Support, Tohoku University, Sendai 980-8577, Japan
c Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
d Institute for Materials Research, Tohoku University, Sendai 980-8577, Japan
Further Information

Publication History

Received 1 August 2011
Publication Date:
19 October 2011 (online)

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Abstract

Nanoporous gold material exhibits a catalytic activity on the benzannulation reaction between ortho-alkynylbenzaldehydes and alkynes. The catalyst is easily recoverable and can be reused several times without leaching and loss of activity.

Key words

nanoporous gold - benzannulation - nanostructures - catalysis - cycloaddition

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15

The catalyst is reusable beyond the second reuse, but the reaction time tends to be longer for completion, probably owing to the gradual coarsening of the porous structure.

16

General Procedure
To a mixture of o-alkynylbenzaldehyde 1 (0.2 mmol) and nanoporous gold (20 mol%) in o-C6H4Cl2 (0.5 mL) was added alkyne compound 2 (1.2 mmol) at r.t. under Ar atmosphere. The mixture was stirred for 2.5 h at 150 ˚C and cooled down to r.t. The liquid moiety was separated by a pipette and evaporated to leave the crude product, which was purified by silica gel column chromatography using hexane-EtOAc as eluent to give the pure product 3. The recovered catalyst was washed with Et2O several times, dried under reduced pressure, and reused without further purification.