Versatile telluracycle synthesis: Via the sequential electrophilic telluration of C(sp2)-Zn and C(sp2)-H bonds

Bin Wu; Melvina; Xiangyang Wu; Edwin Kok Lee Yeow; Naohiko Yoshikai

doi:10.1039/c7sc01162h

Versatile telluracycle synthesis: Via the sequential electrophilic telluration of C(sp²)-Zn and C(sp²)-H bonds

Bin Wu, Melvina, Xiangyang Wu, Edwin Kok Lee Yeow, Naohiko Yoshikai

PHA - Molecular Pharmaceutical Science

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

We report herein a new approach for the synthesis of tellurium-bridged aromatic compounds based on the sequential electrophilic telluration of C(sp²)-Zn and C(sp²)-H bonds with tellurium(iv) chlorides. A combination of transition metal-catalyzed (migratory) arylmetalation of alkynes and sequential telluration allows for the expedient construction of a library of functionalized benzo[b]tellurophenes. Furthermore, a variety of heteroarene-fused benzotellurophenes and other novel tellurium-embedded polycyclic aromatics can be readily synthesized from the corresponding 2-iodoheterobiaryls.

Original language	English
Pages (from-to)	4527-4532
Number of pages	6
Journal	Chemical Science
Volume	8
Issue number	6
DOIs	https://doi.org/10.1039/c7sc01162h
Publication status	Published - 2017

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10.1039/c7sc01162h

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title = "Versatile telluracycle synthesis: Via the sequential electrophilic telluration of C(sp2)-Zn and C(sp2)-H bonds",

abstract = "We report herein a new approach for the synthesis of tellurium-bridged aromatic compounds based on the sequential electrophilic telluration of C(sp2)-Zn and C(sp2)-H bonds with tellurium(iv) chlorides. A combination of transition metal-catalyzed (migratory) arylmetalation of alkynes and sequential telluration allows for the expedient construction of a library of functionalized benzo[b]tellurophenes. Furthermore, a variety of heteroarene-fused benzotellurophenes and other novel tellurium-embedded polycyclic aromatics can be readily synthesized from the corresponding 2-iodoheterobiaryls.",

author = "Bin Wu and Melvina and Xiangyang Wu and {Lee Yeow}, {Edwin Kok} and Naohiko Yoshikai",

note = "Funding Information: This work was supported by the Singapore Ministry of Education (RG 114/15), Nanyang Technological University, and JST, CREST. We thank Dr Yongxin Li and Dr Rakesh Ganguly for assistance with the X-ray crystallographic analysis. Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7sc01162h",

language = "English",

volume = "8",

pages = "4527--4532",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

number = "6",

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TY - JOUR

T1 - Versatile telluracycle synthesis

T2 - Via the sequential electrophilic telluration of C(sp2)-Zn and C(sp2)-H bonds

AU - Wu, Bin

AU - Melvina,

AU - Wu, Xiangyang

AU - Lee Yeow, Edwin Kok

AU - Yoshikai, Naohiko

N1 - Funding Information: This work was supported by the Singapore Ministry of Education (RG 114/15), Nanyang Technological University, and JST, CREST. We thank Dr Yongxin Li and Dr Rakesh Ganguly for assistance with the X-ray crystallographic analysis. Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - We report herein a new approach for the synthesis of tellurium-bridged aromatic compounds based on the sequential electrophilic telluration of C(sp2)-Zn and C(sp2)-H bonds with tellurium(iv) chlorides. A combination of transition metal-catalyzed (migratory) arylmetalation of alkynes and sequential telluration allows for the expedient construction of a library of functionalized benzo[b]tellurophenes. Furthermore, a variety of heteroarene-fused benzotellurophenes and other novel tellurium-embedded polycyclic aromatics can be readily synthesized from the corresponding 2-iodoheterobiaryls.

AB - We report herein a new approach for the synthesis of tellurium-bridged aromatic compounds based on the sequential electrophilic telluration of C(sp2)-Zn and C(sp2)-H bonds with tellurium(iv) chlorides. A combination of transition metal-catalyzed (migratory) arylmetalation of alkynes and sequential telluration allows for the expedient construction of a library of functionalized benzo[b]tellurophenes. Furthermore, a variety of heteroarene-fused benzotellurophenes and other novel tellurium-embedded polycyclic aromatics can be readily synthesized from the corresponding 2-iodoheterobiaryls.

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DO - 10.1039/c7sc01162h

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SN - 2041-6520

VL - 8

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EP - 4532

JO - Chemical Science

JF - Chemical Science

IS - 6

ER -

Versatile telluracycle synthesis: Via the sequential electrophilic telluration of C(sp²)-Zn and C(sp²)-H bonds

Abstract

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