Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst

Hirokazu Tsukamoto; Takamichi Suzuki; Masanori Sato; Yoshinori Kondo

doi:10.1016/j.tetlet.2007.10.001

Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst

Hirokazu Tsukamoto, Takamichi Suzuki, Masanori Sato, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

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

9 Citations (Scopus)

Abstract

Polystyrene-bound diethanolamine (PS-DEAM) work-up for a newly developed Pd(PPh₃)₄-catalyzed cleavage of allylic alkyl ethers using phenylboronic acid can effectively release Pd-free parent alcohols. Furthermore, chromatography-free deallylation can be conducted by using vinylboronic anhydride pyridine complex as an allyl scavenger with a catalytic amount of Pd(OAc)₂ and 4-(diphenylphosphino)benzoic acid instead of Pd(PPh₃)₄ to yield the desired products in high purities and yields after removal of volatile byproducts and the phosphine-derived contaminants by evaporation and sequestration through acid-base interaction with PS-DEAM, respectively.

Original language	English
Pages (from-to)	8438-8441
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2007.10.001
Publication status	Published - 2007 Nov 26

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst",

abstract = "Polystyrene-bound diethanolamine (PS-DEAM) work-up for a newly developed Pd(PPh3)4-catalyzed cleavage of allylic alkyl ethers using phenylboronic acid can effectively release Pd-free parent alcohols. Furthermore, chromatography-free deallylation can be conducted by using vinylboronic anhydride pyridine complex as an allyl scavenger with a catalytic amount of Pd(OAc)2 and 4-(diphenylphosphino)benzoic acid instead of Pd(PPh3)4 to yield the desired products in high purities and yields after removal of volatile byproducts and the phosphine-derived contaminants by evaporation and sequestration through acid-base interaction with PS-DEAM, respectively.",

author = "Hirokazu Tsukamoto and Takamichi Suzuki and Masanori Sato and Yoshinori Kondo",

note = "Funding Information: This work was partly supported by a Grant-in-Aid from the Japan Society for Promotion of Sciences (No. 18790003). ",

year = "2007",

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doi = "10.1016/j.tetlet.2007.10.001",

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journal = "Tetrahedron Letters",

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T1 - Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst

AU - Tsukamoto, Hirokazu

AU - Suzuki, Takamichi

AU - Sato, Masanori

AU - Kondo, Yoshinori

N1 - Funding Information: This work was partly supported by a Grant-in-Aid from the Japan Society for Promotion of Sciences (No. 18790003).

PY - 2007/11/26

Y1 - 2007/11/26

N2 - Polystyrene-bound diethanolamine (PS-DEAM) work-up for a newly developed Pd(PPh3)4-catalyzed cleavage of allylic alkyl ethers using phenylboronic acid can effectively release Pd-free parent alcohols. Furthermore, chromatography-free deallylation can be conducted by using vinylboronic anhydride pyridine complex as an allyl scavenger with a catalytic amount of Pd(OAc)2 and 4-(diphenylphosphino)benzoic acid instead of Pd(PPh3)4 to yield the desired products in high purities and yields after removal of volatile byproducts and the phosphine-derived contaminants by evaporation and sequestration through acid-base interaction with PS-DEAM, respectively.

AB - Polystyrene-bound diethanolamine (PS-DEAM) work-up for a newly developed Pd(PPh3)4-catalyzed cleavage of allylic alkyl ethers using phenylboronic acid can effectively release Pd-free parent alcohols. Furthermore, chromatography-free deallylation can be conducted by using vinylboronic anhydride pyridine complex as an allyl scavenger with a catalytic amount of Pd(OAc)2 and 4-(diphenylphosphino)benzoic acid instead of Pd(PPh3)4 to yield the desired products in high purities and yields after removal of volatile byproducts and the phosphine-derived contaminants by evaporation and sequestration through acid-base interaction with PS-DEAM, respectively.

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Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst

Abstract

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