Letter
Efficient Aqueous-Phase Heck and Suzuki Couplings of Aryl Bromides Using Tri(4,6-dimethyl-3- sulfonatophenyl)phosphine Trisodium Salt (TXPTS)
Purchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract

Sterically demanding, sulfonated arylphosphines TXPTS and TMAPTS have been applied to the aqueous-phase Heck and Suzuki coupling of aryl bromides. TXPTS provides good yields of Heck coupling products from aryl bromides at 80 °C, while both TMAPTS and TPPTS gave significantly less active catalysts. TXPTS is the first ligand to promote the aqueous-phase Heck coupling under such mild conditions. Both TXPTS and TMAPTS provide active catalysts for Suzuki couplings of aryl bromides at 50 °C.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 15 ACS Journal articles (5 most recent appear below).

Water-Soluble Triarylphosphines as Biomarkers for Protein S-Nitrosation
Erika Bechtold, Julie A. Reisz, Chananat Klomsiri, Allen W. Tsang, Marcus W. Wright, Leslie B. Poole, Cristina M. Furdui and S. Bruce KingACS Chemical Biology2010 5 (4), 405-414Water-Soluble Triarylphosphines as Biomarkers for Protein S-Nitrosation
Erika Bechtold, Julie A. Reisz, Chananat Klomsiri, Allen W. Tsang, Marcus W. Wright, Leslie B. Poole, Cristina M. Furdui and S. Bruce KingACS Chemical Biology2010 5 (4), 405-414S-Nitrosothiols (RSNOs) represent an important class of post-translational modifications that preserve and amplify the actions of nitric oxide and regulate enzyme activity. Several regulatory proteins are now verified targets of cellular S-nitrosation, ...

A Convenient Catalyst for Aqueous and Protein Suzuki−Miyaura Cross-Coupling
Justin M. Chalker, Charlotte S. C. Wood and Benjamin G. DavisJournal of the American Chemical Society2009 131 (45), 16346-16347A Convenient Catalyst for Aqueous and Protein Suzuki−Miyaura Cross-Coupling
Justin M. Chalker, Charlotte S. C. Wood and Benjamin G. DavisJournal of the American Chemical Society2009 131 (45), 16346-16347A phosphine-free palladium catalyst for aqueous Suzuki−Miyaura cross-coupling is presented. The catalyst is active enough to mediate hindered, ortho-substituted biaryl couplings but mild enough for use on peptides and proteins. The Suzuki−Miyaura ...

Synthesis, Structures, and Characterizations of [ArTi(O-i-Pr)3]2 and Efficient Room-Temperature Aryl−Aryl Coupling of Aryl Bromides with [ArTi(O-i-Pr)3]2 Catalyzed by the Economic Pd(OAc)2/PCy3 System
Hsu-Tang Yang, Shuangliu Zhou, Feng-Shuo Chang, Chi-Ren Chen and Han-Mou GauOrganometallics2009 28 (19), 5715-5721Synthesis, Structures, and Characterizations of [ArTi(O-i-Pr)3]2 and Efficient Room-Temperature Aryl−Aryl Coupling of Aryl Bromides with [ArTi(O-i-Pr)3]2 Catalyzed by the Economic Pd(OAc)2/PCy3 System
Hsu-Tang Yang, Shuangliu Zhou, Feng-Shuo Chang, Chi-Ren Chen and Han-Mou GauOrganometallics2009 28 (19), 5715-5721The series of aryltris(2-propoxo)titanium reagents [ArTi(O-i-Pr)3]2 (Ar = Ph (1a), 2-MeC6H4 (1b), 4-MeC6H4 (1c), 4-ClC6H4 (1d), 4-TMSC6H4 (1e), 4-CF3C6H4 (1f), 3,5-Me2C6H3 (1g)) was synthesized from reactions of the in situ prepared ClTi(O-i-Pr)3 with ...

Reaction Progress Analysis: Powerful Tool for Understanding Suzuki−Miyaura Reaction and Control of Polychlorobiphenyl Impurity
Sandeep B. Kedia and Mark B. MitchellOrganic Process Research & Development2009 13 (3), 420-428Reaction Progress Analysis: Powerful Tool for Understanding Suzuki−Miyaura Reaction and Control of Polychlorobiphenyl Impurity
Sandeep B. Kedia and Mark B. MitchellOrganic Process Research & Development2009 13 (3), 420-428Cross coupling of unsaturated aryl or vinyl triflates/halides with aryl boronic acids using Pd as catalyst (Suzuki coupling) have become increasingly attractive for making the heterocoupled product (Ar−Ar′). However, most Pd cycle reactions produce some ...

Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions
Kevin H. ShaughnessyChemical Reviews2009 109 (2), 643-710Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions
Kevin H. ShaughnessyChemical Reviews2009 109 (2), 643-710
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue January 22, 2004
- Received October 16, 2003
Cart

ACS
Network






