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Synthesis
DOI: 10.1055/a-2311-4002
review
Dedicated to Prof. H. Ila

ortho-Halobenzyl Halides as Precursors for the Synthesis of Five- to Nine-Membered Ring Structures Employing Transition Metals as Catalysts

Nayyef Aljaar∗
a   Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
,
Majed Shtaiwi
a   Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
,
Basem F. Ali
b   Department of Chemistry, Faculty of Science, Al al-Bayt University, Al-Mafraq 25113, Jordan
,
Mahmoud Al-Refai
b   Department of Chemistry, Faculty of Science, Al al-Bayt University, Al-Mafraq 25113, Jordan
,
Kamal Kant
c   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Ng Shereinai Bliss
c   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Mousa Al-Noaimi
a   Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
d   Department of Chemistry, Faculty of Science, Kuwait University, 13060 Safat, Kuwait
,
Lo'ay Ahmed Al-Momani
a   Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
,
Chandi C. Malakar  ∗
c   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
› Author AffiliationsN.A. gratefully acknowledges the financial and research support from The Hashemite University (Department of Chemistry). C.C.M. is grateful to the Science and Engineering Research Board (SERB), India (CRG/2020/004509 and ECR/2016/000337) for financial support.
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Abstract

This review highlights the multifaceted usefulness of o-halobenzyl halides as pivotal substrates for the construction of five- to nine-membered cyclic structures with the aid of transition metals as catalysts. These privileged entities engage dual active sites, enabling the combination of both intermolecular benzylation and intramolecular arylation strategies that directs the formation of a diverse repository of cyclic structures. The introduction of transition-metal catalysis in cross-coupling transformations sparked a revolution in forging aryl–heteroatom bonds, culminating in the evolution of more potent methodologies for the synthesis of a wide spectrum of valuable compounds. Furthermore, the associated pharmaceutical and biological attributes of these cyclic structures augment their significance in medicinal chemistry research. This review aims to showcase the importance of this synthetic methodology and its far-reaching applications in synthesis.

1 Introduction

2 Synthesis of Five-Membered Rings

3 Synthesis of Six-Membered Rings

4 Synthesis of Seven-Membered Rings

5 Synthesis of Eight- and Nine-Membered Rings

6 Conclusion

Key words

C–N bond formation - C–C bond formation - C–O bond formation - C–S bond formation - o-halobenzyl halides - transition-metal catalysis


Publication History

Received: 10 March 2024

Accepted after revision: 22 April 2024

Accepted Manuscript online:
22 April 2024

Article published online:
16 May 2024

© 2024. Thieme. All rights reserved

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