LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates.
| Autor: | Huang L; University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States., Ackerman LKG; University of Rochester , Rochester , New York 14627 , United States., Kang K; University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States., Parsons AM; University of Rochester , Rochester , New York 14627 , United States., Weix DJ; University of Wisconsin-Madison , Madison , Wisconsin 53706 , United States. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Journal of the American Chemical Society [J Am Chem Soc] 2019 Jul 17; Vol. 141 (28), pp. 10978-10983. Date of Electronic Publication: 2019 Jul 09. |
| DOI: | 10.1021/jacs.9b05461 |
| Abstrakt: | While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|