Site‐Selective C(sp3)−H Borylation of 3‐Azabicyclohexanes by Cooperative Iridium/Aluminum Catalysis

Functionalized 3‐azabicyclo[3.1.0]hexanes are highly interesting for their physiochemical and pharmacological properties. We report an unprecedented direct bridge‐head C(sp3)−H borylation by cooperative iridium/aluminum catalysis. This reaction proceeds under mild conditions in good yields with mode...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2024-02, Vol.13 (2)
Main Authors: Shimazaki, Yuto, Osawa, Ayumi, Nakao, Yoshiaki
Format: Article
Language:English
Subjects:
Aluminum
Catalysis
Chemical synthesis
Hexanes
Iridium
Physiochemistry
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Summary:Functionalized 3‐azabicyclo[3.1.0]hexanes are highly interesting for their physiochemical and pharmacological properties. We report an unprecedented direct bridge‐head C(sp3)−H borylation by cooperative iridium/aluminum catalysis. This reaction proceeds under mild conditions in good yields with moderate to complete site selectivities. Moreover, the use of a BINOL‐based chiral aluminum catalyst renders the synthesis of enantioenriched alkylboronate products. We also disclose its synthetic utility through rapid diversifications without any loss of the stereochemical information.This manuscript is dedicated to Professor Keiji Maruoka on his 70th birthday.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300487