Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters

Jun Sun; Toshiya Yoshiiwa; Takayuki Iwata; Mitsuru Shindo

doi:10.1021/acs.orglett.9b02069

Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters

Jun Sun, Toshiya Yoshiiwa, Takayuki Iwata, Mitsuru Shindo

Department of Fundamental Organic Chemistry

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

6 Citations (Scopus)

Abstract

Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.

Original language	English
Pages (from-to)	6585-6588
Number of pages	4
Journal	Organic letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.9b02069
Publication status	Published - Sept 6 2019

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b02069

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title = "Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters",

abstract = "Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.",

author = "Jun Sun and Toshiya Yoshiiwa and Takayuki Iwata and Mitsuru Shindo",

note = "Funding Information: This work was partially supported by JSPS KAKENHI (nos. JP22390002, JP24106731, JP16H01157, JP26293004, JP17K14449, JP18H04418, JP18H04624, and JP18H02557), the Asahi Glass Foundation (T.I.), and the MEXT Project of “Integrated Research Consortium on Chemical Sciences” (T.I.). This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices.” Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = sep,

day = "6",

doi = "10.1021/acs.orglett.9b02069",

language = "English",

volume = "21",

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journal = "Organic Letters",

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T1 - Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters

AU - Sun, Jun

AU - Yoshiiwa, Toshiya

AU - Iwata, Takayuki

AU - Shindo, Mitsuru

N1 - Funding Information: This work was partially supported by JSPS KAKENHI (nos. JP22390002, JP24106731, JP16H01157, JP26293004, JP17K14449, JP18H04418, JP18H04624, and JP18H02557), the Asahi Glass Foundation (T.I.), and the MEXT Project of “Integrated Research Consortium on Chemical Sciences” (T.I.). This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices.” Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/9/6

Y1 - 2019/9/6

N2 - Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.

AB - Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters

Abstract

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