Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 1, Pages 373-377Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508914
Keywords
alkynes; alkynols; cascade reactions; C-H activation; homogeneous catalysis
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Funding
- NSFC/China [21421004, 21190033, 21172069, 21372072]
- NCET [NCET-13-0798]
- Basic Research Program of the Shanghai Committee of Science and Technology [13M1400802]
- Eastern Scholar Distinguished Professor Program
- Fundamental Research Funds for the Central Universities
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Two tunable cascade reactions of alkynols and alkynes have been developed by combining Sc(OTf)(3) and rhodium catalysis. In the absence of H2O, an endo-cycloisomerization/ C-H activation cascade reaction provided 2,3-dihydronaphtho[1,2-b] furans in good to high yields. In the presence of H2O, the product of alkynol hydration underwent an addition/C-H activation cascade reaction with an alkyne, which led to the formation of 4,5-dihydro-3 H-spiro[furan-2,1'-isochromene] derivatives in good yields under mild reaction conditions. Mechanistic studies of the cascade reactions indicated that the rate-determining step involves C-H bond cleavage and that the hydration of the alkynol plays a key role in switching between the two reaction pathways.
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