Journal of Organic Chemistry, volume 85, issue 10, pages 6359-6371
Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives
Publication type: Journal Article
Publication date: 2020-04-17
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
The first metal-free and facile radical addition/cyclization of simple alcohols with diaryl(arylethynyl)phosphine oxides has been described with azobisisobutyronitrile as a radical initiator, affording an efficient and one-pot procedure to access a new class of hydroxymethyl benzo[b]phosphole oxides and 6H-indeno[2,1-b]phosphindole 5-oxides for potential application in organic materials via sequential C(sp3)-H/C(sp2)-H functionalization. The method employs easily accessible starting materials and is endowed with high regioselectivity and broad functional-group tolerance.
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Guo J. et al. Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives // Journal of Organic Chemistry. 2020. Vol. 85. No. 10. pp. 6359-6371.
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Guo J., Mao C., Deng B., Ye L., Yin Y., Gao Y., Tu S. Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives // Journal of Organic Chemistry. 2020. Vol. 85. No. 10. pp. 6359-6371.
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TY - JOUR
DO - 10.1021/acs.joc.0c00118
UR - https://doi.org/10.1021/acs.joc.0c00118
TI - Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives
T2 - Journal of Organic Chemistry
AU - Guo, Jiami
AU - Mao, Chenlu
AU - Deng, Bin
AU - Ye, Liyi
AU - Yin, Yingwu
AU - Gao, Yu-Xing
AU - Tu, Song
PY - 2020
DA - 2020/04/17
PB - American Chemical Society (ACS)
SP - 6359-6371
IS - 10
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2020_Guo,
author = {Jiami Guo and Chenlu Mao and Bin Deng and Liyi Ye and Yingwu Yin and Yu-Xing Gao and Song Tu},
title = {Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.0c00118},
number = {10},
pages = {6359--6371},
doi = {10.1021/acs.joc.0c00118}
}
Cite this
MLA
Copy
Guo, Jiami, et al. “Azobisisobutyronitrile-Initiated Oxidative C–H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives.” Journal of Organic Chemistry, vol. 85, no. 10, Apr. 2020, pp. 6359-6371. https://doi.org/10.1021/acs.joc.0c00118.