US 11,779,912 B2
Synthesis and characterization of Ru alkylidene complexes
Adam M. Johns, Claremont, CA (US); Jessica R. Herron, Pasadena, CA (US); Richard L. Pederson, San Gabriel, CA (US); Bryan A. Fiamengo, Yorba Linda, CA (US); Jennifer A. Beerman, Monrovia, CA (US); Tzu-Pin Lin, El Lago, TX (US); Crystal K. Chu, Cambridge, MA (US); and Robert H. Grubbs, Pasadena, CA (US)
Assigned to UMICORE AG & Co. KG, Hanau-Wolfgang (DE); and CALIFORNIA INSTITUTE OF TECHNOLOGY, Pasadena, CA (US)
Filed by Umicore AG & Co. KG, Hanau-Wolfgang (DE); and California Institute of Technology, Pasadena, CA (US)
Filed on Aug. 27, 2021, as Appl. No. 17/459,089.
Application 17/459,089 is a division of application No. 16/919,704, filed on Jul. 2, 2020, granted, now 11,123,722.
Application 16/919,704 is a division of application No. 16/341,635, granted, now 10,792,651, previously published as PCT/US2017/056919, filed on Oct. 17, 2017.
Claims priority of provisional application 62/509,269, filed on May 22, 2017.
Claims priority of provisional application 62/410,003, filed on Oct. 19, 2016.
Prior Publication US 2021/0394167 A1, Dec. 23, 2021
Int. Cl. B01J 31/24 (2006.01); B01J 31/22 (2006.01); C07F 15/00 (2006.01)
CPC B01J 31/2414 (2013.01) [B01J 31/2208 (2013.01); B01J 31/2273 (2013.01); B01J 31/2278 (2013.01); B01J 31/2295 (2013.01); B01J 31/2404 (2013.01); B01J 31/2409 (2013.01); C07F 15/0046 (2013.01); B01J 2231/543 (2013.01); B01J 2531/821 (2013.01)] 2 Claims
 
1. A method of synthesizing an olefin metathesis catalyst represented by the structure of Formula (C)

OG Complex Work Unit Chemistry
the method comprising contacting an olefin metathesis catalyst represented by the structure of Formula (IVa)

OG Complex Work Unit Chemistry
with a N-Heterocyclic Carbene ligand of formula

OG Complex Work Unit Chemistry
at, wherein:
X1 and X2 are independently halogen, trifluoroacetate, per-fluorophenols or nitrate;
R1 is unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —NRC1-C6 alkylene)(C5-C24 aryl)]2;
R2 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
R3 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle or substituted saturated N-heterocycle;
R5 and R6 are independently hydrogen, unsubstituted C5-C24 aryl, or substituted C5-C24 aryl;
generally R5 and R6 are independently substituted C5-C24 aryl with one to three unsubstituted (C1-C6 alkyl) groups or substituted (C1-C6 alkyl) groups.