Transition-metal-free and base promoted C-C bond formation C-N bond cleavage of organoammonium salts

A transition-metal-free and base promoted C-C bond forming reaction of benzyl C(sp 3 )-H bond with organoammonium salts via C-N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl ammonium salt could couple readily with various benzyl C(sp 3 )-H species, producing the correspo...

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Published in:Organic & biomolecular chemistry 2021-10, Vol.19 (38), p.8237-824
Main Authors: Zhang, Tao, Wang, Kunyu, Ke, Yuting, Tang, Yuanyuan, Liu, Long, Huang, Tianzeng, Li, Chunya, Tang, Zhi, Chen, Tieqiao
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Summary:A transition-metal-free and base promoted C-C bond forming reaction of benzyl C(sp 3 )-H bond with organoammonium salts via C-N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl ammonium salt could couple readily with various benzyl C(sp 3 )-H species, producing the corresponding products in moderate to excellent yields with good functional group tolerance. Late stage chemical manipulation enabled the specific 1,2-diarylethane structure of products transformed into useful olefin compounds via dehydrogenation, which further demonstrated the utility of this reaction. Only mediated by KO t Bu, a deaminative carbon-carbon bond forming reaction of organoammonium salts with benzyl C(sp 3 )-H bond was developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01468d