Iridium-catalyzed hydrocarboxylation of 1,1-dimethylallene: Byproduct-free reverse prenylation of carboxylic acids

Su Kim In; Michael J. Krische

doi:10.1021/ol702914p

Iridium-catalyzed hydrocarboxylation of 1,1-dimethylallene: Byproduct-free reverse prenylation of carboxylic acids

Su Kim In
, Michael J. Krische

University of Texas at Austin

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

60 Scopus citations

Abstract

Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [Ir(COd)Cl]₂ and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.

Original language	English
Pages (from-to)	513-515
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	3
DOIs	https://doi.org/10.1021/ol702914p
State	Published - 7 Feb 2008
Externally published	Yes

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title = "Iridium-catalyzed hydrocarboxylation of 1,1-dimethylallene: Byproduct-free reverse prenylation of carboxylic acids",

abstract = "Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [Ir(COd)Cl]2 and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92\% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.",

author = "In, \{Su Kim\} and Krische, \{Michael J.\}",

year = "2008",

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doi = "10.1021/ol702914p",

language = "English",

volume = "10",

pages = "513--515",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Iridium-catalyzed hydrocarboxylation of 1,1-dimethylallene

T2 - Byproduct-free reverse prenylation of carboxylic acids

AU - In, Su Kim

AU - Krische, Michael J.

PY - 2008/2/7

Y1 - 2008/2/7

N2 - Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [Ir(COd)Cl]2 and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.

AB - Exposure of carboxylic acids 1a-12a to commercially available 1,1-dimethylallene in the presence of substoichiometric quantities of an iridium catalyst prepared in situ from [Ir(COd)Cl]2 and BIPHEP provides the corresponding 1,1-dimethylallyl (reverse prenyl) esters 1b-12b in 74-92% isolated yield. This protocol represents the first branch-regioselective allene hydrocarboxylation. Stoichiometric byproducts are not generated in this process and protecting groups are not required for alcohols, phenols, and indolic amines.

UR - https://www.scopus.com/pages/publications/38949093789

U2 - 10.1021/ol702914p

DO - 10.1021/ol702914p

M3 - Article

C2 - 18181640

AN - SCOPUS:38949093789

SN - 1523-7060

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SP - 513

EP - 515

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Iridium-catalyzed hydrocarboxylation of 1,1-dimethylallene: Byproduct-free reverse prenylation of carboxylic acids

Abstract

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