Cobalt-Catalyzed Direct C–H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine

Mingliang Li; Jun Joelle Wang

doi:10.1021/acs.orglett.8b02812

Cobalt-Catalyzed Direct C–H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine

Mingliang Li, Jun Joelle Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

44 Citations (Scopus)

Abstract

A direct C(sp²)–H thiolation of aromatic amides with disulfides was developed. The coupling reaction proceeds between the thioether radical and cobaltacycle intermediate. This method exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that the cobalt(IV) intermediate is probably formed during the course of the reaction. The thiolation product can be transformed to Quetiapine, which is an atypical antipsychotic agent approved for the treatment of schizophrenia and bipolar disorder.

Original language	English
Pages (from-to)	6490–6493
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	20
Early online date	4 Oct 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02812
Publication status	Published - 19 Oct 2018

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10.1021/acs.orglett.8b02812

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title = "Cobalt-Catalyzed Direct C–H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine",

abstract = "A direct C(sp2)–H thiolation of aromatic amides with disulfides was developed. The coupling reaction proceeds between the thioether radical and cobaltacycle intermediate. This method exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that the cobalt(IV) intermediate is probably formed during the course of the reaction. The thiolation product can be transformed to Quetiapine, which is an atypical antipsychotic agent approved for the treatment of schizophrenia and bipolar disorder.",

author = "Mingliang Li and Wang, {Jun Joelle}",

note = "Funding information: This work is supported by Shenzhen Basic Research Program (JCYJ20170817112532779 and JCYJ20170412152435366) and the Shenzhen Nobel Prize Scientists Laboratory Project (C17783101). Publisher copyright: {\textcopyright} 2018 American Chemical Society",

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doi = "10.1021/acs.orglett.8b02812",

language = "English",

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journal = "Organic Letters",

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TY - JOUR

T1 - Cobalt-Catalyzed Direct C–H Thiolation of Aromatic Amides with Disulfides

T2 - Application to the Synthesis of Quetiapine

AU - Li, Mingliang

AU - Wang, Jun Joelle

N1 - Funding information: This work is supported by Shenzhen Basic Research Program (JCYJ20170817112532779 and JCYJ20170412152435366) and the Shenzhen Nobel Prize Scientists Laboratory Project (C17783101). Publisher copyright: © 2018 American Chemical Society

PY - 2018/10/19

Y1 - 2018/10/19

N2 - A direct C(sp2)–H thiolation of aromatic amides with disulfides was developed. The coupling reaction proceeds between the thioether radical and cobaltacycle intermediate. This method exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that the cobalt(IV) intermediate is probably formed during the course of the reaction. The thiolation product can be transformed to Quetiapine, which is an atypical antipsychotic agent approved for the treatment of schizophrenia and bipolar disorder.

AB - A direct C(sp2)–H thiolation of aromatic amides with disulfides was developed. The coupling reaction proceeds between the thioether radical and cobaltacycle intermediate. This method exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that the cobalt(IV) intermediate is probably formed during the course of the reaction. The thiolation product can be transformed to Quetiapine, which is an atypical antipsychotic agent approved for the treatment of schizophrenia and bipolar disorder.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000448488200038?SID=EUW1ED0B743XgiqgGYM6z5SHHSCuT

U2 - 10.1021/acs.orglett.8b02812

DO - 10.1021/acs.orglett.8b02812

M3 - Journal article

SN - 1523-7060

VL - 20

SP - 6490

EP - 6493

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Cobalt-Catalyzed Direct C–H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine

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