Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 15, Pages 4320-4323Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700539
Keywords
azides; boron; reaction mechanisms; rhodium; synthetic methods
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Funding
- National Natural Science Foundation of China [21672256, 21302219]
- National S&T Pillar Program of China [2015BAK45B01]
- Chinese Universities Scientific Fund [2016RC040]
- Beijing National Laboratory of Molecular Sciences (BNLMS)
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Amidine is a notable nitrogen-containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)-catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N-sulfonyl-, N-acyl-, and N-phosphoryl-functionalized, as well as general N-aryl and N-alkyl amidines with broad substrate scope. In addition, functionalized guanidines can also been synthesized when amines are used instead. The accomplishment of estrone-derived amidine and glibenclamide bioisosteres further reveals the practical utility of this strategy.
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