Lossen Rearrangement vs C–N Reductive Elimination Enabled by Rh(III)-Catalyzed C–H Activation/Selective Lactone Ring-Opening: Chemodivergent Synthesis of Quinolinones and Dihydroisoquinolinones
Тип публикации: Journal Article
Дата публикации: 2020-12-04
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
33274634
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
An unprecedented Rh(III)-catalyzed cascade C-H activation/Lossen rearrangement of aromatic amides with methyleneoxetanones has been realized along with a tunable C-N bond reductive elimination/trans esterification, giving divergent access to quinolinones and dihydroisoquinolinones via selective ring-opening of the four-membered lactone unit. Combined computational and experimental mechanistic studies defined the solvent-involved distinguished reaction paths, the origin of the observed chemodivergence, as well as the role of the substituent attached at the oxidizing directing group in tuning the reaction outcomes.
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Bian M. et al. Lossen Rearrangement vs C–N Reductive Elimination Enabled by Rh(III)-Catalyzed C–H Activation/Selective Lactone Ring-Opening: Chemodivergent Synthesis of Quinolinones and Dihydroisoquinolinones // Organic Letters. 2020. Vol. 22. No. 24. pp. 9677-9682.
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Bian M., Mawjuda H., Gao H., Xu H., Zhou Z., Yi W. Lossen Rearrangement vs C–N Reductive Elimination Enabled by Rh(III)-Catalyzed C–H Activation/Selective Lactone Ring-Opening: Chemodivergent Synthesis of Quinolinones and Dihydroisoquinolinones // Organic Letters. 2020. Vol. 22. No. 24. pp. 9677-9682.
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TY - JOUR
DO - 10.1021/acs.orglett.0c03734
UR - https://doi.org/10.1021/acs.orglett.0c03734
TI - Lossen Rearrangement vs C–N Reductive Elimination Enabled by Rh(III)-Catalyzed C–H Activation/Selective Lactone Ring-Opening: Chemodivergent Synthesis of Quinolinones and Dihydroisoquinolinones
T2 - Organic Letters
AU - Bian, Mengyao
AU - Mawjuda, Hamdulla
AU - Gao, Hui
AU - Xu, Huiying
AU - Zhou, Zhi
AU - Yi, Wei
PY - 2020
DA - 2020/12/04
PB - American Chemical Society (ACS)
SP - 9677-9682
IS - 24
VL - 22
PMID - 33274634
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2020_Bian,
author = {Mengyao Bian and Hamdulla Mawjuda and Hui Gao and Huiying Xu and Zhi Zhou and Wei Yi},
title = {Lossen Rearrangement vs C–N Reductive Elimination Enabled by Rh(III)-Catalyzed C–H Activation/Selective Lactone Ring-Opening: Chemodivergent Synthesis of Quinolinones and Dihydroisoquinolinones},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.0c03734},
number = {24},
pages = {9677--9682},
doi = {10.1021/acs.orglett.0c03734}
}
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MLA
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Bian, Mengyao, et al. “Lossen Rearrangement vs C–N Reductive Elimination Enabled by Rh(III)-Catalyzed C–H Activation/Selective Lactone Ring-Opening: Chemodivergent Synthesis of Quinolinones and Dihydroisoquinolinones.” Organic Letters, vol. 22, no. 24, Dec. 2020, pp. 9677-9682. https://doi.org/10.1021/acs.orglett.0c03734.