Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Improved Catalysts for Ethenolysis Reactions

摘要

Described herein are compounds and methods of catalyzing ethenolysis reactions, optionally on an industrial scale. In certain embodiments, the catalysts bear cyclic alkyl amino carbene (CAAC) ligands with an ortho substituent, such as a methyl substituent, on an N-aryl ring. When used to catalyze ethenolysis reactions, certain such compounds produce a turnover number greater than 50,000.

主权项

1. A compound, wherein the compound is
(A) a compound of Formula I: wherein, independently for each occurrence, X is, independently for each occurrence, alkoxy or halo; R2 is, independently for each occurrence, alkyl; R3 is alkyl; R4 is alkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl; or R3 and R4, taken together with the carbon atom to which they are attached, form a five-, six-, or ten-membered cycloalkyl or heterocyclyl ring; R5 is alkyl; R6 is H or alkyl, provided that (i) R5 and R6 are not the same, and (ii) R6 has fewer atoms than R5; and R2 is alkyl; (B) a compound of Formula II: wherein, independently for each occurrence, X is, independently for each occurrence, alkoxy or halo; R2 is, independently for each occurrence, alkyl; R3 is alkyl; R4 is alkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl; or R3 and R4, taken together with the carbon atom to which they are attached, form a five-, six-, or ten-membered cycloalkyl or heterocyclyl ring; R5 is, independently for each occurrence, alkyl; and R7 is alkyl; (C) a compound of Formula III: wherein, independently for each occurrence, X is, independently for each occurrence, alkoxy or halo; R2 is alkyl; R3 is alkyl; R5 is, independently for each occurrence, alkyl; R7 is alkyl; and R8 is aryl or heteroaryl; or (D) a compound of Formula IV: wherein, independently for each occurrence, X is, independently for each occurrence, alkoxy or halo; R2 is alkyl; R3 is alkyl; R5 is, independently for each occurrence, alkyl; R7 is alkyl; and R9 is C2-C6 alkyl; or R3 and R9, taken together with the carbon atom to which they are attached, form a five-, or ten-membered cycloalkyl or heterocyclyl ring.