Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides

Zheng Yang; Wen Juan Hao; Shu Liang Wang; Jin Peng Zhang; Bo Jiang; Guigen Li; Shu Jiang Tu

doi:10.1021/acs.joc.5b01684

Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides

Zheng Yang, Wen Juan Hao, Shu Liang Wang, Jin Peng Zhang, Bo Jiang, Guigen Li, Shu Jiang Tu

Chemistry and Biochemistry

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

73 Scopus citations

Abstract

A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.

Original language	English
Pages (from-to)	9224-9230
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	80
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.5b01684
State	Published - Sep 18 2015

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title = "Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides",

abstract = "A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.",

author = "Zheng Yang and Hao, {Wen Juan} and Wang, {Shu Liang} and Zhang, {Jin Peng} and Bo Jiang and Guigen Li and Tu, {Shu Jiang}",

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doi = "10.1021/acs.joc.5b01684",

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T1 - Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides

AU - Yang, Zheng

AU - Hao, Wen Juan

AU - Wang, Shu Liang

AU - Zhang, Jin Peng

AU - Jiang, Bo

AU - Li, Guigen

AU - Tu, Shu Jiang

PY - 2015/9/18

Y1 - 2015/9/18

N2 - A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.

AB - A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.

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ER -

Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides

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