Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control
Publication type: Journal Article
Publication date: 2013-11-08
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract
Copper-catalyzed coupling reaction of 2-io- dobenzoic acids and alkynes such as terminal acety- lenes, alkynyl carboxylic acids, and trimethylsilylace- tylene selectively afforded isocoumarins and phthal- A in the presence of cesium carbonate (Cs2CO3) and dimethyl sulfoxide (DMSO). Among the regio- selective products, only the 6-endo-dig product, iso- coumarin, was formed at 1008C, and the 5-exo-dig product, phthalide, was formed as a major product at 258C. A variety of alkynes produced the correspond- ing isocoumarins and phthalides in good yields. A mechanism is suggested in which the formation of 2- alkynylbenzoic acid as an intermediate via Sonoga- shira-type coupling was ruled out in the reaction pathway.
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68
Total citations:
68
Citations from 2024:
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(10.29%)
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GOST
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Kumar M. R. et al. Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control // Advanced Synthesis and Catalysis. 2013. Vol. 355. No. 16. pp. 3221-3230.
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Kumar M. R., Irudayanathan F. M., Moon J. H., Lee S. Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control // Advanced Synthesis and Catalysis. 2013. Vol. 355. No. 16. pp. 3221-3230.
Cite this
RIS
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TY - JOUR
DO - 10.1002/adsc.201300561
UR - https://doi.org/10.1002/adsc.201300561
TI - Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control
T2 - Advanced Synthesis and Catalysis
AU - Kumar, Manian Rajesh
AU - Irudayanathan, Francis Mariaraj
AU - Moon, Joong Ho
AU - Lee, Sunwoo
PY - 2013
DA - 2013/11/08
PB - Wiley
SP - 3221-3230
IS - 16
VL - 355
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2013_Kumar,
author = {Manian Rajesh Kumar and Francis Mariaraj Irudayanathan and Joong Ho Moon and Sunwoo Lee},
title = {Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control},
journal = {Advanced Synthesis and Catalysis},
year = {2013},
volume = {355},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/adsc.201300561},
number = {16},
pages = {3221--3230},
doi = {10.1002/adsc.201300561}
}
Cite this
MLA
Copy
Kumar, Manian Rajesh, et al. “Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control.” Advanced Synthesis and Catalysis, vol. 355, no. 16, Nov. 2013, pp. 3221-3230. https://doi.org/10.1002/adsc.201300561.