Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation | Zendy

Geraint H. M. Davies | Zendy; Matthieu Jouffroy | Zendy; Fatemeh Sherafat | Zendy; Borna Saeednia | Zendy; Casey Howshall | Zendy; Gary A. Molander | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation

Author(s) -

Geraint H. M. Davies,

Matthieu Jouffroy,

Fatemeh Sherafat,

Borna Saeednia,

Casey Howshall,

Gary A. Molander

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b01331

Subject(s) - chemistry , regioselectivity , diversification (marketing strategy) , chemical space , stereochemistry , organic chemistry , biochemistry , drug discovery , catalysis , business , marketing

Methods for the regioselective C-H borylation and subsequent cross-coupling of the 2,1-borazaronaphthalene core are reported. Azaborines are dependent on B-N/C═C isosterism when employed in strategies for developing diverse heterocyclic scaffolds. Although 2,1-borazaronaphthalene is closely related to naphthalene in terms of structure, the argument is made that the former has electronic similarities to indole. Based on that premise, iridium-mediated C-H activation has enabled facile installation of a versatile, nucleophilic coupling handle at a previously inaccessible site of 2,1-borazaronaphthalenes. A variety of substituted 2,1-borazaronaphthalene cores can be successfully borylated and further cross-coupled in a facile manner to yield diverse C(8)-substituted 2,1-borazaronaphthalenes.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research