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Shedding Light on the Diverse Reactivity of NacNacAl with N‐Heterocycles.

Authors :
Dmitrienko, Anton
Pilkington, Melanie
Britten, James F.
Gabidullin, Bulat M.
Est, Art
Nikonov, Georgii I.
Source :
Angewandte Chemie. 9/7/2020, Vol. 132 Issue 37, p16281-16287. 7p.
Publication Year :
2020

Abstract

The aluminum(I) compound NacNacAl (NacNac=[ArNC(Me)CHC(Me)NAr]−, Ar=2,6‐iPr2C6H3, 1) shows diverse and substrate‐controlled reactivity in reactions with N‐heterocycles. 4‐Dimethylaminopyridine (DMAP), a basic substrate in which the 4‐position is blocked, induces rearrangement of NacNacAl by shifting a hydrogen atom from the methyl group of the NacNac backbone to the aluminum center. In contrast, C−H activation of the methyl group of 4‐picoline takes place to produce a species with a reactive terminal methylene. Reaction of 1 with 3,5‐lutidine results in the first example of an uncatalyzed, room‐temperature cleavage of an sp2 C−H bond (in the 4‐position) by an AlI species. Another reactivity mode was observed for quinoline, which undergoes 2,2′‐coupling. Finally, the reaction of 1 with phthalazine produces the product of N−N bond cleavage. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00448249
Volume :
132
Issue :
37
Database :
Academic Search Index
Journal :
Angewandte Chemie
Publication Type :
Academic Journal
Accession number :
145533512
Full Text :
https://doi.org/10.1002/ange.202005925