Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur

Mieko Arisawa; Masanori Ashikawa; Atsushi Suwa; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2005.01.069

Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur

Mieko Arisawa, Masanori Ashikawa, Atsushi Suwa, Masahiko Yamaguchi

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

29 Citations (Scopus)

Abstract

Rhodium complexes RhH(PPh₃)₄ and Rh(acac)(CH ₂CH₂)₂ catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity.

Original language	English
Pages (from-to)	1727-1729
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2005.01.069
Publication status	Published - Mar 7 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.01.069

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title = "Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur",

abstract = "Rhodium complexes RhH(PPh3)4 and Rh(acac)(CH 2CH2)2 catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity.",

author = "Mieko Arisawa and Masanori Ashikawa and Atsushi Suwa and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by grants from the Japan Society of Promotion of Science (Nos. 14207094 and 16109001). M.A. thanks support from NEDO of Japan (No. 02A44003d).",

year = "2005",

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doi = "10.1016/j.tetlet.2005.01.069",

language = "English",

volume = "46",

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journal = "Tetrahedron Letters",

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T1 - Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur

AU - Arisawa, Mieko

AU - Ashikawa, Masanori

AU - Suwa, Atsushi

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by grants from the Japan Society of Promotion of Science (Nos. 14207094 and 16109001). M.A. thanks support from NEDO of Japan (No. 02A44003d).

PY - 2005/3/7

Y1 - 2005/3/7

N2 - Rhodium complexes RhH(PPh3)4 and Rh(acac)(CH 2CH2)2 catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity.

AB - Rhodium complexes RhH(PPh3)4 and Rh(acac)(CH 2CH2)2 catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity.

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DO - 10.1016/j.tetlet.2005.01.069

M3 - Article

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SN - 0040-4039

VL - 46

SP - 1727

EP - 1729

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur

Abstract

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