ArticleAngewandte Chemie (International ed. in English)2026
Atroposelective Suzuki-Miyaura Coupling to Form 2-Amino-2'-Hydroxybiphenyls Enabled by sRuPhos.
Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- Diastereomer Resolution and Structural-Property Relationship of Phosphorus-Chirogenic Luminescent α-Aminophosphaphenanthrenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Chiral Spiro-Scaffolded C(spAngewandte Chemie (International ed. in English) · 2026Article
- Optimization of a Resolution Process Allowing Access to Both Enantiomers of the Versatile Chiral Phosphine Ligand sSPhos on Scale.Organic process research & development · 2026Article
- Atroposelective Bromination for the Synthesis of Chiral Biaryl Phosphines via Cross-Assembled Catalysis with Chiral Phosphoric Acid and Achiral Phenol.Journal of the American Chemical Society · 2026Article
- The acylative kinetic resolution of 1,2-azaborine naphthols.Chemical science · 2026Article
- Installing Axial Chirality by Atroposelective C(spJournal of the American Chemical Society · 2026Article
- Atroposelective Suzuki-Miyaura Coupling to Form 2-Amino-2'-Hydroxybiphenyls Enabled by sRuPhos.Angewandte Chemie (International ed. in English) · 2026Article
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Abstract
Atropisomeric biaryls are increasingly important in molecules of pharmaceutical interest. Asymmetric versions of the Suzuki-Miyaura coupling arguably constitute the most direct and attractive route to these without resorting to wasteful preparative separations or resolution steps. Herein, we report a new chiral phosphine ligand sRuPhos, a sulfonated form of RuPhos, which permits the coupling of unprotected ortho-bromoanilines and ortho-phenolic boronate esters with extremely high ee (up to 99%) to form 2-amino-2'-hydroxybiphenyls. N-alkylation can be accommodated on the aniline nitrogen and sRuPhos is also able to form highly hindered 2,2'-biphenols, which could not be achieved in our previous studies using the related chiral ligand sSPhos. Given the great importance of biaryl atropisomers in medicinal chemistry, as well as the potential utility of the 2-amino-2'-hydroxybiphenyl motif in chiral catalyst design, we anticipate that this reaction will soon find utility and that sRuPhos may be a useful ligand in the development of other asymmetric palladium-catalysed processes.
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