American Chemical Society (ACS)
Organic Letters
,  volume 20 ,  issue 13 ,  pages 3892-3896

2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade.

Publication type: Journal Article
Publication date: 2018-06-13
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An efficient and redox-neutral synthesis of 2 H-chromene-3-carboxylic acids from N-phenoxyacetamides and methyleneoxetanones has been realized via a solvent-controlled and rhodium(III)-catalyzed C-H activation/unusual [3 + 3] annulation sequence. This transformation represents the first example of using an α-methylene-β-lactone unit as the three-carbon source in transition-metal-catalyzed C-H activations through selective alkyl C-O bond cleavage. Synthetic applications and mechanistic details, including further derivatization of 2 H-chromene-3-carboxylic acids, the isolation and identification of a five-membered rhodacycle, as well as the theoretical studies for reasoning a plausible Rh(III)-Rh(V)-Rh(III) process, have also been discussed.
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GOST Copy
Zhou Z. et al. 2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade. // Organic Letters. 2018. Vol. 20. No. 13. pp. 3892-3896.
GOST all authors (up to 50) Copy
Zhou Z., Bian M., Zhao L., Gao H., HUANG J., Liu X., Xiyong Yu., Li X., Yi W. 2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade. // Organic Letters. 2018. Vol. 20. No. 13. pp. 3892-3896.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b01477
UR - https://doi.org/10.1021/acs.orglett.8b01477
TI - 2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade.
T2 - Organic Letters
AU - Zhou, Zhi
AU - Bian, Mengyao
AU - Zhao, Lixin
AU - Gao, Hui
AU - HUANG, JUNJUN
AU - Liu, Xiawen
AU - Xiyong, Yu
AU - Li, Xingwei
AU - Yi, Wei
PY - 2018
DA - 2018/06/13
PB - American Chemical Society (ACS)
SP - 3892-3896
IS - 13
VL - 20
PMID - 29897772
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Zhou,
author = {Zhi Zhou and Mengyao Bian and Lixin Zhao and Hui Gao and JUNJUN HUANG and Xiawen Liu and Yu Xiyong and Xingwei Li and Wei Yi},
title = {2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade.},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.8b01477},
number = {13},
pages = {3892--3896},
doi = {10.1021/acs.orglett.8b01477}
}
MLA
Cite this
MLA Copy
Zhou, Zhi, et al. “2 H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 3] Annulation Cascade..” Organic Letters, vol. 20, no. 13, Jun. 2018, pp. 3892-3896. https://doi.org/10.1021/acs.orglett.8b01477.