Base-Mediated Annulation\nof <i>ortho</i>-Iminophenols and <i>ortho</i>-Vinylphenols\nwith MBH Carbonates\nof Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran\nDerivatives

We\nhave developed a convenient synthetic protocol for efficient\nconstruction of significant dihydrobenzofuran and benzofuran scaffolds\nby Lewis base-mediated annulation reaction <i>ortho</i>-iminophenols\nand <i>ortho</i>-vinylphenols with MBH carbonates of isatins\nunder mild and metal-free conditions. The selective generation of\ndifferent kinds of dihydrobenzofuran and benzofuran derivatives was\nsuccessfully achieved by employing different substituted isatin-derived\nMBH carbonates with <i>ortho</i>-<i>N</i>-tosyliminophenols\nand <i>ortho</i>-vinylphenols. The features included broad\nsubstrate scopes, excellent functional group compatibility, high molecular\ndiversity, and atomic economy.

Publication Details

Journal
Figshare
Published
2024-10-15
DOI
https://doi.org/10.1021/acs.joc.4c01501.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Base-Mediated Annulation\nof ortho-Iminophenols and ortho-Vinylphenols\nwith MBH Carbonates\nof Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran\nDerivatives

Figshare
Catalytic C–H Functionalization Methods
article

Base-Mediated Annulation\nof ortho-Iminophenols and ortho-Vinylphenols\nwith MBH Carbonates\nof Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran\nDerivatives

article en

Abstract

We\nhave developed a convenient synthetic protocol for efficient\nconstruction of significant dihydrobenzofuran and benzofuran scaffolds\nby Lewis base-mediated annulation reaction <i>ortho</i>-iminophenols\nand <i>ortho</i>-vinylphenols with MBH carbonates of isatins\nunder mild and metal-free conditions. The selective generation of\ndifferent kinds of dihydrobenzofuran and benzofuran derivatives was\nsuccessfully achieved by employing different substituted isatin-derived\nMBH carbonates with <i>ortho</i>-<i>N</i>-tosyliminophenols\nand <i>ortho</i>-vinylphenols. The features included broad\nsubstrate scopes, excellent functional group compatibility, high molecular\ndiversity, and atomic economy.

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Catalytic C–H Functionalization Methods
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