Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation

Guilherme A M Jardim; John F. Bower; Eufrânio N. Da Silva Júnior

doi:10.1021/acs.orglett.6b01586

Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation

Guilherme A M Jardim, John F. Bower^*, Eufrânio N. Da Silva Júnior

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

52 Citations (Scopus)

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Abstract

Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.

Original language	English
Pages (from-to)	4454-4457
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	18
Early online date	7 Sept 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b01586
Publication status	Published - 16 Sept 2016

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01586. Please refer to any applicable terms of use of the publisher.
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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01586. Please refer to any applicable terms of use of the publisher.
Final published version, 2.56 MBLicence: CC BY-NC

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title = "Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation",

abstract = "Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.",

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doi = "10.1021/acs.orglett.6b01586",

language = "English",

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journal = "Organic Letters",

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T1 - Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles

T2 - C-H Iodination, Bromination, and Phenylselenation

AU - Jardim, Guilherme A M

AU - Bower, John F.

AU - Da Silva Júnior, Eufrânio N.

PY - 2016/9/16

Y1 - 2016/9/16

N2 - Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.

AB - Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.

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U2 - 10.1021/acs.orglett.6b01586

DO - 10.1021/acs.orglett.6b01586

M3 - Article (Academic Journal)

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AN - SCOPUS:84988452261

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation

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Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation

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