Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach

Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach

2,4-Dibromophenyl benzoate (3) was synthesized via Steglich esterification. The derivatives of 2, 4-dibromophenyl benzoate (3) with electron withdrawing and donating aryl-boronic acids were prepared with good yields via palladium catalyzed Suzuki Miyaura reaction. DFT calculations were also implemen...

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Published in:Journal of Molecular Structure
Main Author: Imran H.M.; Rasool N.; Kanwal I.; Hashmi M.A.; Altaf A.A.; Ahmed G.; Malik A.; Kausar S.; Ud-Din Khan S.; Ahmad A.; Ali Shah S.A.
Format: Article
Language:English
Published: Elsevier B.V. 2020
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85087873670&doi=10.1016%2fj.molstruc.2020.128839&partnerID=40&md5=e280809431d47632017fc818342382d8
id 2-s2.0-85087873670
spelling 2-s2.0-85087873670
Imran H.M.; Rasool N.; Kanwal I.; Hashmi M.A.; Altaf A.A.; Ahmed G.; Malik A.; Kausar S.; Ud-Din Khan S.; Ahmad A.; Ali Shah S.A.
Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
2020
Journal of Molecular Structure
1222

10.1016/j.molstruc.2020.128839
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85087873670&doi=10.1016%2fj.molstruc.2020.128839&partnerID=40&md5=e280809431d47632017fc818342382d8
2,4-Dibromophenyl benzoate (3) was synthesized via Steglich esterification. The derivatives of 2, 4-dibromophenyl benzoate (3) with electron withdrawing and donating aryl-boronic acids were prepared with good yields via palladium catalyzed Suzuki Miyaura reaction. DFT calculations were also implemented on the newly synthesized ester products to probe into their electronic structure and reactivity descriptors. According to DFT studies, compound 6c showed maximum reactivity while 4 showed maximum stability in the series. Furthermore, the values of Hyperpolarizability showed that the synthesized compounds have potential as moderate molecular nonlinear optical (NLO) materials. © 2020 Elsevier B.V.
Elsevier B.V.
222860
English
Article
author Imran H.M.; Rasool N.; Kanwal I.; Hashmi M.A.; Altaf A.A.; Ahmed G.; Malik A.; Kausar S.; Ud-Din Khan S.; Ahmad A.; Ali Shah S.A.
spellingShingle Imran H.M.; Rasool N.; Kanwal I.; Hashmi M.A.; Altaf A.A.; Ahmed G.; Malik A.; Kausar S.; Ud-Din Khan S.; Ahmad A.; Ali Shah S.A.
Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
author_facet Imran H.M.; Rasool N.; Kanwal I.; Hashmi M.A.; Altaf A.A.; Ahmed G.; Malik A.; Kausar S.; Ud-Din Khan S.; Ahmad A.; Ali Shah S.A.
author_sort Imran H.M.; Rasool N.; Kanwal I.; Hashmi M.A.; Altaf A.A.; Ahmed G.; Malik A.; Kausar S.; Ud-Din Khan S.; Ahmad A.; Ali Shah S.A.
title Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
title_short Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
title_full Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
title_fullStr Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
title_full_unstemmed Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
title_sort Synthesis of halogenated [1,1′-biphenyl]-4-yl benzoate and [1,1′:3′,1″- terphenyl]-4′-yl benzoate by palladium catalyzed cascade C–C coupling and structural analysis through computational approach
publishDate 2020
container_title Journal of Molecular Structure
container_volume 1222
container_issue
doi_str_mv 10.1016/j.molstruc.2020.128839
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85087873670&doi=10.1016%2fj.molstruc.2020.128839&partnerID=40&md5=e280809431d47632017fc818342382d8
description 2,4-Dibromophenyl benzoate (3) was synthesized via Steglich esterification. The derivatives of 2, 4-dibromophenyl benzoate (3) with electron withdrawing and donating aryl-boronic acids were prepared with good yields via palladium catalyzed Suzuki Miyaura reaction. DFT calculations were also implemented on the newly synthesized ester products to probe into their electronic structure and reactivity descriptors. According to DFT studies, compound 6c showed maximum reactivity while 4 showed maximum stability in the series. Furthermore, the values of Hyperpolarizability showed that the synthesized compounds have potential as moderate molecular nonlinear optical (NLO) materials. © 2020 Elsevier B.V.
publisher Elsevier B.V.
issn 222860
language English
format Article
accesstype
record_format scopus
collection Scopus
_version_ 1809678482199805952

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