Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp<SUP>3</SUP>)-H Functionalization Cascades



Jing, Changcheng, Jones, Benjamin T, Adams, Ross J and Bower, John F ORCID: 0000-0002-7551-8221
(2022) Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp<SUP>3</SUP>)-H Functionalization Cascades. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 144 (37). pp. 16749-16754.

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Abstract

Unique examples of aza-Heck-based C(sp<sup>3</sup>)-H functionalization cascades are described. Under Pd(0)-catalyzed conditions, the aza-Heck-type cyclization of <i>N</i>-(pentafluorobenzoyloxy)carbamates generates alkyl-Pd(II) intermediates that effect C(sp<sup>3</sup>)-H palladation en route to cyclopropanes. Key factors that control the site selectivity of the cyclopropanation process have been elucidated such that selective access to a wide range of ring- or spiro-fused systems can be achieved.

Item Type: Article
Uncontrolled Keywords: Carbamates, Cyclopropanes, Cyclization, Catalysis
Divisions: Faculty of Science and Engineering > School of Physical Sciences
Depositing User: Symplectic Admin
Date Deposited: 27 Sep 2022 08:58
Last Modified: 18 Oct 2023 01:26
DOI: 10.1021/jacs.2c08304
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3164887