Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 1, Pages 195-202Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja408185c
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Funding
- National Institute of General Medical Sciences, National Institutes of Health [GM-087620]
- National Science Foundation [CHE-0848982, CHE-1302043]
- Swedish Research Council (VR)
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1302043] Funding Source: National Science Foundation
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Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereo-selectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including a-allenyl ketones and amino-substituted heterocycles.
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