Frustrated Lewis\nPair-Mediated Cycloisomerization\nof Propargylaniline and Aryl Propargyl Ether Derivatives via a 6-<i>endo</i>-dig Cyclization/Dehydrogenation Sequence

An efficient FLP-mediated cycloisomerization\nis described, providing\n easy access to quinolinium and chromenylium derivatives by treatment\nof readily available propargylanilines and aryl propargyl ethers with\nLewis acidic boranes, respectively. The reaction proceeds via a 6-<i>endo</i>-dig cyclization/dehydrogenation sequence. The heteroatom\nfunctions serve as Lewis bases in combination with Lewis acidic boranes\nto effect synergistic activation of an alkynyl triple bond and a C–H\nbond.

Publication Details

Journal
Figshare
Published
2024-11-20
DOI
https://doi.org/10.1021/acs.orglett.4c03817.s001
Primary Topic
Organoboron and organosilicon chemistry
Type
article
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article

Frustrated Lewis\nPair-Mediated Cycloisomerization\nof Propargylaniline and Aryl Propargyl Ether Derivatives via a 6-endo-dig Cyclization/Dehydrogenation Sequence

Figshare
Organoboron and organosilicon chemistry
article

Frustrated Lewis\nPair-Mediated Cycloisomerization\nof Propargylaniline and Aryl Propargyl Ether Derivatives via a 6-endo-dig Cyclization/Dehydrogenation Sequence

article en

Abstract

An efficient FLP-mediated cycloisomerization\nis described, providing\n easy access to quinolinium and chromenylium derivatives by treatment\nof readily available propargylanilines and aryl propargyl ethers with\nLewis acidic boranes, respectively. The reaction proceeds via a 6-<i>endo</i>-dig cyclization/dehydrogenation sequence. The heteroatom\nfunctions serve as Lewis bases in combination with Lewis acidic boranes\nto effect synergistic activation of an alkynyl triple bond and a C–H\nbond.

Figshare
Clean water and sanitation
Openalex Percentile: Top 76%
Organoboron and organosilicon chemistry
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Frustrated Lewis\nPair-Mediated Cycloisomerization\nof Propargylaniline and Aryl Propargyl Ether Derivatives via a 6-<i>endo</i>-dig Cyclization/Dehydrogenation Sequence · Figshare (2024) | TGRS Research Map | TGRS