期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 26, 页码 6508-6512出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901150
关键词
chemoselective coupling; cross-coupling; functionalized Grignard reagents; Pd-PEPPSI; sequential coupling
资金
- NSERC (Canada)
- Lilly Research Award Program (LRAP)
We report a general and rapid chemoselective Kumada-Tamao-Corriu (KTC) cross-coupling of aryl bromides in the presence of chlorides or triflates with functionalized Grignard reagents at 0 degrees C in 15 min by using Pd-PEPPSI-IPent(Cl) (C4). Nucleophiles and electrophiles (or both) can contain Grignard-sensitive functional groups (-CN, -COOR, etc.). Control experiments together with DFT calculations suggest that transmetallation is rate limiting for the selective cross-coupling of Br in the presence of Cl/OTf with functionalized Grignard reagents. One-pot sequential KTC/KTC cross-couplings with bromo-chloro arenes have been demonstrated for the first time. We also report the one-pot sequential KTC/Negishi cross-couplings using C4 showcasing the versatility of this methodology.
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