Regio- and Stereospecific Preparation of β-(Alkylthio)alkenyl-1,3,2-benzodioxaboroles by Nickel-Catalyzed Hydroboration of Thioacetylenes with Catecholborane

Ilya D. Gridnev; Norio Miyaura; Akira Suzuki

doi:10.1021/om00026a053

Regio- and Stereospecific Preparation of β-(Alkylthio)alkenyl-1,3,2-benzodioxaboroles by Nickel-Catalyzed Hydroboration of Thioacetylenes with Catecholborane

Ilya D. Gridnev, Norio Miyaura, Akira Suzuki

Research output: Contribution to journal › Comment/debate › peer-review

85 Citations (Scopus)

Abstract

Hydroboration of 1-(alkylthio)-1-alkynes with catecholborane 1 in the presence of 3 mol % of NiCl₂(dppe) or NiCl₂(dppp) proceeds regio-and stereospecifically, giving excellent yields of [(E)-1-(alkylthio)-1-alken-2-yl]-1,3,2-benzodioxaboroles 2 under mild conditions.

Original language	English
Pages (from-to)	589-592
Number of pages	4
Journal	Organometallics
Volume	12
Issue number	2
DOIs	https://doi.org/10.1021/om00026a053
Publication status	Published - 1993 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Regio- and Stereospecific Preparation of β-(Alkylthio)alkenyl-1,3,2-benzodioxaboroles by Nickel-Catalyzed Hydroboration of Thioacetylenes with Catecholborane",

abstract = "Hydroboration of 1-(alkylthio)-1-alkynes with catecholborane 1 in the presence of 3 mol % of NiCl2(dppe) or NiCl2(dppp) proceeds regio-and stereospecifically, giving excellent yields of [(E)-1-(alkylthio)-1-alken-2-yl]-1,3,2-benzodioxaboroles 2 under mild conditions.",

author = "Gridnev, {Ilya D.} and Norio Miyaura and Akira Suzuki",

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journal = "Organometallics",

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T1 - Regio- and Stereospecific Preparation of β-(Alkylthio)alkenyl-1,3,2-benzodioxaboroles by Nickel-Catalyzed Hydroboration of Thioacetylenes with Catecholborane

AU - Gridnev, Ilya D.

AU - Miyaura, Norio

AU - Suzuki, Akira

PY - 1993/1/1

Y1 - 1993/1/1

N2 - Hydroboration of 1-(alkylthio)-1-alkynes with catecholborane 1 in the presence of 3 mol % of NiCl2(dppe) or NiCl2(dppp) proceeds regio-and stereospecifically, giving excellent yields of [(E)-1-(alkylthio)-1-alken-2-yl]-1,3,2-benzodioxaboroles 2 under mild conditions.

AB - Hydroboration of 1-(alkylthio)-1-alkynes with catecholborane 1 in the presence of 3 mol % of NiCl2(dppe) or NiCl2(dppp) proceeds regio-and stereospecifically, giving excellent yields of [(E)-1-(alkylthio)-1-alken-2-yl]-1,3,2-benzodioxaboroles 2 under mild conditions.

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JF - Organometallics

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ER -

Regio- and Stereospecific Preparation of β-(Alkylthio)alkenyl-1,3,2-benzodioxaboroles by Nickel-Catalyzed Hydroboration of Thioacetylenes with Catecholborane

Abstract

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