US 12,448,404 B2
Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis
Krzysztof Skowerski, Jablonowo Pomorskie (PL); and Rafal Gawin, Warsaw (PL)
Assigned to Apeiron Synthesis S.A., Wroclaw (PL)
Filed by APEIRON SYNTHESIS S.A., Wroclaw (PL)
Filed on Nov. 11, 2024, as Appl. No. 18/943,268.
Application 18/943,268 is a division of application No. 18/234,753, filed on Aug. 16, 2023, granted, now 12,173,015.
Application 18/234,753 is a division of application No. 17/513,752, filed on Oct. 28, 2021, granted, now 11,976,085, issued on May 7, 2024.
Application 17/513,752 is a continuation of application No. 15/764,123, granted, now 11,192,911, issued on Dec. 7, 2021, previously published as PCT/IB2016/054486, filed on Jul. 27, 2016.
Claims priority of application No. 414234 (PL), filed on Sep. 30, 2015.
Prior Publication US 2025/0066402 A1, Feb. 27, 2025
Int. Cl. C07F 15/00 (2006.01); B01J 31/22 (2006.01); C07C 6/02 (2006.01)
CPC C07F 15/0046 (2013.01) [B01J 31/2208 (2013.01); B01J 31/2273 (2013.01); B01J 31/2278 (2013.01); B01J 31/2295 (2013.01); C07C 6/02 (2013.01); B01J 2231/54 (2013.01); B01J 2231/543 (2013.01); B01J 2531/821 (2013.01); B01J 2540/44 (2013.01); C07C 2531/22 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A compound represented by the Formula 1,

OG Complex Work Unit Chemistry
wherein:
X1 and X2 are each independently an anionic ligand selected from halogen, —CN, —SCN, —OR′, —SR′, —O(C—O)R′, —O(SO2)R′, or —OSi(R′)3, wherein R′ is C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C5-C20 aryl, each of which is optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C5-C20 heteroaryloxy, or halogen;
Z is selected from the group consisting of O, S, NR′, wherein R′ is C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C5-C20 aryl, which are optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C5-C20 heteroaryloxy, or halogen;
Ar is an aryl group substituted with hydrogen atoms or optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, and C5-C20 heteroaryloxy group, or halogen;
R1 and R2 are each independently hydrogen, C1-C25 alkyl, C1-C25 alkoxy, C2-C25 alkenyl, C1-C12 perfluoroalkyl, C5-C20 aryl, C5-C24 aryloxy, C5-C20 heteroaryloxy; or R1 and R2 are combined together to form a substituted or unsubstituted C4-C10 cyclic or C4-C12 polycyclic system; or an ester (—COOR′), amide (—CONR′2), formyl (—CHO), ketone (—COR′), or hydroxamic (—CON(OR′)(R′)) group, in which R′ is C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C5-C20 aryl, each of which is optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C5-C20 heteroaryloxy, or halogen;
at least one of R3, R4, R5, Re is a phosphonate group (—P(O)(OR′)2), phosphinate group (—P(O)R′(OR′)), phosphonium group (—P(OR′)2), phosphine group (—PR′2), nitro group (—NO2), nitroso group (—NO), carboxy group (—COOH), ester group (—COOR′), formyl group (—CHO), ketone group (—COR′), wherein R′ is C1-C5 alkyl, C1-C5 perfluoroalkyl, C5-C24 aryl, C7-C24 aralkyl, or C5-C24 perfluoroaryl and the remainder of R3, R4, R5, R6 are hydrogen atoms; and
R7, R8, R9, and R10 are each independently hydrogen atom, or C1-C25 alkyl; or R7 and R8, R7 and R9, R8 and R10, or R9 and R10 are combined to form a cyclic system; or independently C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C5-C20 aryl, C1-C5 perfluoroalkyl, C7-C24 aralkyl, C5-C24 perfluoroaryl, each of which is optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C5-C20 heteroaryloxy, or halogen.