Hemilabile Benzyl Ether Enables γ-C(sp 3 )-H Carbonylation and Olefination of Alcohols.
| Autor: | Tanaka K; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Ewing WR; Discovery Chemistry , Bristol-Myers Squibb , P.O. Box 4000, Princeton , New Jersey 08543 , United States., Yu JQ; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States. |
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| Jazyk: | angličtina |
| Zdroj: | Journal of the American Chemical Society [J Am Chem Soc] 2019 Oct 02; Vol. 141 (39), pp. 15494-15497. Date of Electronic Publication: 2019 Sep 18. |
| DOI: | 10.1021/jacs.9b08238 |
| Abstrakt: | Pd-catalyzed C(sp 3 )-H activation of alcohol typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct γ- or δ-C-H carbonylation and olefination of alcohols. The utility of this approach is also demonstrated in the late-stage C-H functionalization of β-estradiol to rapidly prepare desired analogues that required multi-step syntheses with classical methods. |
| Databáze: | MEDLINE |
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