Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

Kota Ishitobi; Kei Muto; Junichiro Yamaguchi

doi:10.1021/acscatal.9b04212

Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

Kota Ishitobi, Kei Muto, Junichiro Yamaguchi^*

^*Corresponding author for this work

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

26 Citations (Scopus)

Abstract

A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient "sulfur source" for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.

Original language	English
Pages (from-to)	11685-11690
Number of pages	6
Journal	ACS Catalysis
Volume	9
Issue number	12
DOIs	https://doi.org/10.1021/acscatal.9b04212
Publication status	Published - 2019 Dec 6

Keywords

N-tosylhydrazone
Pd-carbene
catalytic reaction
thioester
thioether

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.9b04212

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title = "Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones",

abstract = "A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient {"}sulfur source{"} for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.",

keywords = "N-tosylhydrazone, Pd-carbene, catalytic reaction, thioester, thioether",

author = "Kota Ishitobi and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP19H02726, JP18H04272 (to J.Y.), JP18H04661 (Hybrid Catalysis), and JP19K15573 (to K.M.). We thank Cassandra Lim for help the preparation of N -tosylhydrazones. The Materials Characterization Central Laboratory in Waseda University is acknowledged for HRMS measurement. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = dec,

day = "6",

doi = "10.1021/acscatal.9b04212",

language = "English",

volume = "9",

pages = "11685--11690",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

AU - Ishitobi, Kota

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP19H02726, JP18H04272 (to J.Y.), JP18H04661 (Hybrid Catalysis), and JP19K15573 (to K.M.). We thank Cassandra Lim for help the preparation of N -tosylhydrazones. The Materials Characterization Central Laboratory in Waseda University is acknowledged for HRMS measurement. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/12/6

Y1 - 2019/12/6

N2 - A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient "sulfur source" for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.

AB - A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient "sulfur source" for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.

KW - N-tosylhydrazone

KW - Pd-carbene

KW - catalytic reaction

KW - thioester

KW - thioether

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DO - 10.1021/acscatal.9b04212

M3 - Article

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SN - 2155-5435

VL - 9

SP - 11685

EP - 11690

JO - ACS Catalysis

JF - ACS Catalysis

IS - 12

ER -

Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

Abstract

Keywords

ASJC Scopus subject areas

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