Conformationally restricted sulfonate based phosphine ligands for hindered suzuki coupling reactions

A water-soluble phosphorous ligand of formula (I) and racemates, enantiomers, atrop-diastereomers and pharmaceutical salts thereof, for a Pd-catalyzed sterically hindered Suzuki-Miyaura Coupling reaction in aqueous media:

• wherein, R is (C1-C6)-alkyl, CF3, (C3-C10)-carbocyclyl, (5 to 11-membered)heterocarbocyclyl, (C6-C10)aryl, (5 to 11-membered)heteroaryl, ferrocenyl, wherein each such carbocyclyl, heterocarbocyclyl, aryl, ferrocenyl or heteroaryl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of H, —O—(C1-C6)alkyl, (C1-C6)alkyl, and CF3;
• P* is a chiral centre;
• Y is O, S, CH2, NRa, SO2Rb,
• wherein Ra is alkyl, aryl, heteroaryl, acyl preferably tert-butylacyl;
• further wherein Rb is alkyl, aryl, heteroaryl;
• R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is each independently selected from a group consisting of H, halo, CF3, a sulfonyl moiety, (C1-C6)-alkyl, —O—(C1-C6)-alkyl, (C6-C10)aryl, —O—(C6-C10)aryl, (C5-C11) heteroaryl, —O—(C5-C10) heteroaryl, wherein each such alkyl, aryl or heteroaryl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of H, (C1-C6)-alkyl, halo, —O—(C1-C6)alkyl and CF3;
• further wherein, at least any one of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is essentially a sulfonyl moiety of formula (X)
• wherein R11 is —O or N or a metal atom;
• further substituted with a substituent selected from a group consisting of H, a metal atom, substituted or unsubstituted (C1-C6)alkyl, substituted or unsubstituted (C6-C10)aryl, substituted or unsubstituted (C5-C11)heteroaryl, NRxRyRz, (C1-C6)alkyl-NRxRyRz;
• further wherein,
• said metal atom is an alkali metal atom, preferably Li, Na, K, Cs;
• and
• each one of Rx, Ry and Rz is H, halo, CF3, (C1-C6)-alkyl, —O—(C1-C6)-alkyl, (C6-C10)aryl, (C5-C11) heteroaryl, —O—(C5-C11) heteroaryl
• or
• Rx, Ry and Rz taken together with the adjacent N atom can form a 5-11 membered heterocylic ring system which can further be substituted with H, (C1-C6)-alkyl, halo, —O—(C1-C6)alkyl and CF3.