Boron-mediated one-pot access to salicylaldehydes <i>via ortho</i> -C–H hydroxylation of benzaldehydes

Боросодержащий однофазный доступ к салицидальдегидам через орто-C–H гидроксилирование бензальдегидов
Feng Xu, Boya Feng, Ruiyang Wang, Yu Chen
2024-01-01

benzaldehydesone-pot synthesisortho-C–H hydroxylationsalicylaldehydestransient imine-directed borylation
-C-H hydroxylation of benzaldehydes. Directed by a transient imine group, the borylation of benzaldehydes, sequentially followed by the hydroxylation, furnishes diverse salicylaldehydes in a one-pot manner. The resultant salicylaldehydes could be readily applied in the downstream synthesis to produce bioactive molecules.
1
A novel one-pot protocol enables ortho-C–H hydroxylation of benzaldehydes to produce salicylaldehydes.
2
Resulting salicylaldehydes are readily applicable to downstream syntheses to produce bioactive molecules.
3
Sequential borylation followed by hydroxylation in the same reaction vessel furnishes diverse salicylaldehydes.
4
The method uses a transient imine directing group to guide borylation of benzaldehydes prior to hydroxylation.

Benzaldehydes undergoing boron-mediated one-pot ortho-C–H hydroxylation (via transient imine-directed borylation followed by hydroxylation)

Development and demonstration of a transient imine-directed, boron-mediated one-pot sequence (borylation then hydroxylation) to convert benzaldehydes into salicylaldehydes

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2024-01-01
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Authors
Feng Xu
Boya Feng
Ruiyang Wang
Yu Chen
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