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Published on: February 20, 2020
1,3-C-H bond activation on a transient gallium(I)/isocyanate adduct
Sruthi S Puthiyaveetil1, Aishabibi Kassymbek1, Anton Dmitrienko1
1Chemistry Department, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, Ontario, L2S 3A1, Canada. gnikonov@brocku.ca.
Abstract:
Reaction of NacNacGa with phenylisocyante generates a transient species amenable to unusual 1,3-C-H bond addition of unactivated sp3 C-H and sp2 C-H bonds of substrates featuring a hard donor atom. This reaction proceeds for pyridine oxide, dimethylsulfoxide, and dimethylacetamide, but not for pyridine, cyclohexanone, and ethyl acetate. C-H activation was also not observed for reactions with triethylphosphine oxide but, interestingly, in the presence of this compound isocyanate undergoes self-coupling on Ga(I) with a regioselectivity that is different when carried out in the absence of Et3PO.
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