Advertisement

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

Carbenes Made Easy

New route to versatile azavinyl reactive species eschews unstable reagents

by Carmen Drahl
February 15, 2010 | A version of this story appeared in Volume 88, Issue 7

Chemists have found a straightforward way to make rhodium azavinyl carbenes, a new family of reactive species for organic synthesis. To complement the existing tool kit of carbenes, which are high-energy intermediates capable of selective reactions, Valery V. Fokin and coworkers at Scripps Research Institute recently developed tunable azavinyl carbenes with unique synthetic capabilities (J. Am. Chem. Soc. 2009, 131, 18034). But making them involves sulfonyl azides and diazo compounds, which require very careful handling. Fokin, Neil Grimster, and Li Zhang have now devised a new route that gets around the hazardous compounds. From stable NH-triazoles, the one-pot procedure generates carbenes using triflic anhydride, a pyridine base, and a rhodium catalyst (J. Am. Chem. Soc., DOI: 10.1021/ja910187s). The rhodium azavinyl carbenes react with alkenes, yielding cyclopropanes or dihydropyrroles with good stereoselectivity. Avoiding potentially hazardous compounds “could greatly enhance the commercial and large-scale applications of rhodium carbenoid chemistry,” says Huw M. L. Davies, who studies carbenes at Emory University.

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.