Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 29, Pages 7624-7628Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404543
Keywords
arenes; azo compounds; gold; reduction; supported catalysts
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Funding
- National Natural Science Foundation of China [21073042, 21273044]
- State Key Basic Research Program of PRC [2009CB623506]
- Research Fund for the Doctoral Program of Higher Education [2012007000011]
- Science & Technology Commission of Shanghai Municipality [08DZ2270500]
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The azo linkage is a prominent chemical motif which has found numerous applications in materials science, pharmaceuticals, and agrochemicals. Described herein is a sustainable heterogeneous-gold-catalyzed synthesis of azo arenes. Available nitroarenes are deoxygenated and linked selectively by the formation of N=N bonds using molecular H-2 without any external additives. As a result of a unique and remarkable synergy between the metal and support, a facile surface-mediated condensation of nitroso and hydroxylamine intermediates is enabled, and the desired transformation proceeds in a highly selective manner under mild reaction conditions. The protocol tolerates a large variety of functional groups and offers a general and versatile method for the environmentally friendly synthesis of symmetric or asymmetric aromatic azo compounds.
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