Aza-<i>ortho</i>-Quinone Methide Promoted\nStrain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into\nFunctionalized Azetidines

A strategy for activating azabicyclo[1.1.0]butane (ABB)\nwith <i>in situ</i> generated aza-<i>ortho</i>-quinone methide,\npromoted by HFIP, is reported. This unified activation, <i>vis-à-vis</i> strain-release-driven N/C3-functionalization, features a new means\nto prepare functionalized azetidines from ABB. Additionally, the newly\ninstalled motif on azetidine nitrogen could be forged into an indoline <i>via</i> Pd-catalyzed hydroamination, leveraging access to medicinally\nrelevant scaffolds.

Publication Details

Journal
Figshare
Published
2024-10-25
DOI
https://doi.org/10.1021/acs.orglett.4c03577.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Aza-ortho-Quinone Methide Promoted\nStrain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into\nFunctionalized Azetidines

Figshare
Catalytic C–H Functionalization Methods
article

Aza-ortho-Quinone Methide Promoted\nStrain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into\nFunctionalized Azetidines

article en

Abstract

A strategy for activating azabicyclo[1.1.0]butane (ABB)\nwith <i>in situ</i> generated aza-<i>ortho</i>-quinone methide,\npromoted by HFIP, is reported. This unified activation, <i>vis-à-vis</i> strain-release-driven N/C3-functionalization, features a new means\nto prepare functionalized azetidines from ABB. Additionally, the newly\ninstalled motif on azetidine nitrogen could be forged into an indoline <i>via</i> Pd-catalyzed hydroamination, leveraging access to medicinally\nrelevant scaffolds.

Figshare
Openalex Percentile: Top 79%
Catalytic C–H Functionalization Methods
DOISourceOpenAlex
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Aza-<i>ortho</i>-Quinone Methide Promoted\nStrain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into\nFunctionalized Azetidines · Figshare (2024) | TGRS Research Map | TGRS