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Issue 13, 2018
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A borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water

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Abstract

We demonstrate a greener borrowing hydrogen methodology using the π-benzylpalladium system, which offers an efficient and environmentally friendly dehydrative N-monobenzylation of 2-aminopyridines with benzylic alcohols in the absence of base. The crossover experiment using benzyl-α,α-d2 alcohol and 3-methylbenzyl alcohol afforded H/D scrambled products, suggesting that the dehydrative N-benzylation in our catalytic system involves a borrowing hydrogen pathway. KIE experiments show that C–H bond cleavage at the benzylic position of benzyl alcohol is involved in the rate-determining step (KIE = 2.9). This simple base-free protocol can be achieved under mild conditions in an atom-economic process, affording the desired products in moderate to excellent yields.

Graphical abstract: A borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water

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Publication details

The article was received on 02 Apr 2018, accepted on 02 Jun 2018 and first published on 06 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC01028E
Citation: Green Chem., 2018,20, 3044-3049
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    A borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water

    H. Hikawa, H. Imamura, S. Kikkawa and I. Azumaya, Green Chem., 2018, 20, 3044
    DOI: 10.1039/C8GC01028E

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