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Molecular editing of aza-arene C–H bonds by distance, geometry and chirality
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Molecular editing of aza-arene C–H bonds by distance, geometry and chirality
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Journal Article
Molecular editing of aza-arene C–H bonds by distance, geometry and chirality
2022
Overview
Direct molecular editing of heteroarene carbon–hydrogen (C–H) bonds through consecutive selective C–H functionalization has the potential to grant rapid access into diverse chemical spaces, which is a valuable but often challenging venture to achieve in medicinal chemistry
1
. In contrast to electronically biased heterocyclic C–H bonds
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–
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, remote benzocyclic C–H bonds on bicyclic aza-arenes are especially difficult to differentiate because of the lack of intrinsic steric/electronic biases
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–
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. Here we report two conceptually distinct directing templates that enable the modular differentiation and functionalization of adjacent remote (C6 versus C7) and positionally similar (C3 versus C7) positions on bicyclic aza-arenes through careful modulation of distance, geometry and previously unconsidered chirality in template design. This strategy enables direct C–H olefination, alkynylation and allylation at adjacent C6 and C7 positions of quinolines in the presence of a competing C3 position that is spatially similar to C7. Notably, such site-selective, iterative and late-stage C–H editing of quinoline-containing pharmacophores can be performed in a modular fashion in different orders to suit bespoke synthetic applications. This Article, in combination with previously reported complementary methods, now fully establishes a unified late-stage ‘molecular editing’ strategy to directly modify bicyclic aza-arenes at any given site in different orders.
A unified catalytic remote-directing template strategy enabled precise differentiation of remote and adjacent C6–H and C7–H bonds, and similar C3–H and C7–H bonds of a pharmaceutically relevant bicyclic aza-arene scaffold.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
