4.7 Article

Rhodium-Catalyzed Chemo- and Regioselective Intermolecular Cross-Cyclotrimerization of Nonactivated Terminal and Internal Alkynes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 20, Pages 11117-11125

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02121

Keywords

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Funding

  1. ACT-C from Japan Science and Technology Agency (JST, Japan) [JPMJCR1122YR]
  2. Japan Society for the Promotion of Science (JSPS, Japan) [15E103775, JP26102004]
  3. Grants-in-Aid for Scientific Research [26102004, 15H03775] Funding Source: KAKEN

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It has been established that a cationic rhodium(I)/BIPHEP complex is able to catalyze the unprecedented intermolecular cross-cyclotrimerization of nonactivated terminal and: internal alkynes at room temperature. In this transformation, the use, of arylacetylenes as terminal alkynes and 1,4-butynediol derivatives as internal alkynes afforded the cross-cyclotrimerization products with good chemo- and regioselectivity. The present study clearly demonstrated that an electronically biased combination of nonactivated and electron-deficient alkynes is not necessary to realize good chemo- and regioselectivity in the cationic rhodium(I) complex-catalyzed intermolecular cross-cyclotrimerization.

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