One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8

Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K2CO3 in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na2S2O8. The obtained 3-bromo-4-phenylcoumari...

Full description

Bibliographic Details
Main Authors: Teppei Sasaki, Katsuhiko Moriyama, Hideo Togo
Format: Article
Language:English
Published: Beilstein-Institut 2018-02-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
3-aryl-2-propynoic acid
bromo-cyclization
coumarin
diaryliodonium triflate
O-phenylation
Online Access:https://doi.org/10.3762/bjoc.14.22
id doaj-d73b2cd9e3e34e178aeb28de84169248
record_format Article
spelling doaj-d73b2cd9e3e34e178aeb28de841692482021-02-02T01:38:40ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-02-0114134535310.3762/bjoc.14.221860-5397-14-22One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8Teppei Sasaki0Katsuhiko Moriyama1Hideo Togo2Department of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, JapanDepartment of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, JapanDepartment of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, JapanVarious 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K2CO3 in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na2S2O8. The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C–H, C–S, C–N, and C–C bonds at 3-position.https://doi.org/10.3762/bjoc.14.223-aryl-2-propynoic acidbromo-cyclizationcoumarindiaryliodonium triflateO-phenylation
collection DOAJ
language English
format Article
sources DOAJ
author Teppei Sasaki
Katsuhiko Moriyama
Hideo Togo
spellingShingle Teppei Sasaki
Katsuhiko Moriyama
Hideo Togo
One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8
Beilstein Journal of Organic Chemistry
3-aryl-2-propynoic acid
bromo-cyclization
coumarin
diaryliodonium triflate
O-phenylation
author_facet Teppei Sasaki
Katsuhiko Moriyama
Hideo Togo
author_sort Teppei Sasaki
title One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8
title_short One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8
title_full One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8
title_fullStr One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8
title_full_unstemmed One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8
title_sort one-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, tbab, and na2s2o8
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2018-02-01
description Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K2CO3 in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na2S2O8. The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C–H, C–S, C–N, and C–C bonds at 3-position.
topic 3-aryl-2-propynoic acid
bromo-cyclization
coumarin
diaryliodonium triflate
O-phenylation
url https://doi.org/10.3762/bjoc.14.22
work_keys_str_mv AT teppeisasaki onepotpreparationof4aryl3bromocoumarinsfrom4aryl2propynoicacidswithdiaryliodoniumsaltstbabandna2s2o8
AT katsuhikomoriyama onepotpreparationof4aryl3bromocoumarinsfrom4aryl2propynoicacidswithdiaryliodoniumsaltstbabandna2s2o8
AT hideotogo onepotpreparationof4aryl3bromocoumarinsfrom4aryl2propynoicacidswithdiaryliodoniumsaltstbabandna2s2o8
_version_ 1724311415437656064

Similar Items