ADVERTISEMENT
2 /3 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

One-Pot Method Produces Pyrroles

Reaction converts aromatic alkynes to heterocycles in presence of palladium catalyst

by Elizabeth K. Wilson
January 17, 2011 | APPEARED IN VOLUME 89, ISSUE 3

A new synthetic method simplifies the production of 2,4-disubstituted pyrrole heterocycles—an important class of structures common in the chemistry of natural products and pharmaceuticals. Barry M. Trost and colleagues at Stanford University have been developing one-pot reactions of substituted alkynes to create important organic building blocks—an efficient strategy that maximizes atom economy. In this most recent case, Trost’s group, which includes Jean-Philip Lumb and Joseph M. Azzarelli, describes the synthesis of a number of 2,4-disubstituted pyrroles (shown), which were prepared from various substituted aromatic alkynes in the presence of a palladium catalyst (J. Am. Chem. Soc., DOI: 10.1021/ja110117g). The process is tolerant to moisture and air and can be carried out at room temperature. The authors also report that intermediates produced during the reaction can be captured and further functionalized to species such as 2,3,4-trisubstituted pyrroles and 3-substituted pyrrolidin-2-ones.

X

Article:

This article has been sent to the following recipient:

Leave A Comment

*Required to comment