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Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions

Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions
Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions
A new class of sterically hindered phosphines based on a phospha-adamantane framework is described. Arylation or alkylation of the 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phospha-adamantane system allows for the preparation of tertiary phosphines suitable for use in palladium-catalyzed cross-coupling reactions. For example, use of a catalytic system incorporating Pd2(dba)3 and 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phospha-adamantane is shown to promote the Suzuki cross-coupling of aryl iodides, bromides, and activated chlorides with a variety of aryl boronic acids at room temperature in a few hours with high yields.
arylboronic acids, organic electrophiles, chlorides, amination, complexes, catalysts
1523-7060
953-955
Adjabeng, George
58a6bdb0-3f0c-4742-af7c-1be1c2f8006c
Brenstrum, Tim
78a90308-d1b1-4d59-a6eb-ae8bbf691e3d
Wilson, Jeffrey
4280de05-05f5-4a3a-bdb4-c0553def794a
Frampton, Christopher
29dcdaec-296b-4ebd-9a51-8b9679722b42
Robertson, Al
7e4344c8-f5d6-4374-bcf9-0f2b84fc0c7e
Hillhouse, John
6dfda6c4-e12a-4a28-9dfb-844fcda92aa4
McNulty, James
4f9c7e1e-6e24-4939-99e6-7a4aae31bd54
Capretta, Alfredo
ec840cba-f217-4b53-b846-b83ea8697fb3
Adjabeng, George
58a6bdb0-3f0c-4742-af7c-1be1c2f8006c
Brenstrum, Tim
78a90308-d1b1-4d59-a6eb-ae8bbf691e3d
Wilson, Jeffrey
4280de05-05f5-4a3a-bdb4-c0553def794a
Frampton, Christopher
29dcdaec-296b-4ebd-9a51-8b9679722b42
Robertson, Al
7e4344c8-f5d6-4374-bcf9-0f2b84fc0c7e
Hillhouse, John
6dfda6c4-e12a-4a28-9dfb-844fcda92aa4
McNulty, James
4f9c7e1e-6e24-4939-99e6-7a4aae31bd54
Capretta, Alfredo
ec840cba-f217-4b53-b846-b83ea8697fb3

Adjabeng, George, Brenstrum, Tim, Wilson, Jeffrey, Frampton, Christopher, Robertson, Al, Hillhouse, John, McNulty, James and Capretta, Alfredo (2003) Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions. Organic Letters, 5 (6), 953-955. (doi:10.1021/ol0341647).

Record type: Article

Abstract

A new class of sterically hindered phosphines based on a phospha-adamantane framework is described. Arylation or alkylation of the 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phospha-adamantane system allows for the preparation of tertiary phosphines suitable for use in palladium-catalyzed cross-coupling reactions. For example, use of a catalytic system incorporating Pd2(dba)3 and 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phospha-adamantane is shown to promote the Suzuki cross-coupling of aryl iodides, bromides, and activated chlorides with a variety of aryl boronic acids at room temperature in a few hours with high yields.

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Published date: 20 March 2003
Keywords: arylboronic acids, organic electrophiles, chlorides, amination, complexes, catalysts

Identifiers

Local EPrints ID: 19875
URI: https://eprints.soton.ac.uk/id/eprint/19875
ISSN: 1523-7060
PURE UUID: 1dee685c-22d4-4786-86f3-5e57e7ab0937

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Date deposited: 22 Feb 2006
Last modified: 15 Jul 2019 19:26

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Contributors

Author: George Adjabeng
Author: Tim Brenstrum
Author: Jeffrey Wilson
Author: Christopher Frampton
Author: Al Robertson
Author: John Hillhouse
Author: James McNulty
Author: Alfredo Capretta

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