US2022119433A1PendingUtilityA1

Synthesis of biaryl ketones and biaryl diketones via carbonylative suzuki-miyaura coupling reactions catalyzed by bridged bis(n-heterocyclic carbene)palladium(ii) catalysts

Assignee: UNIV KING FAHD PET & MINERALSPriority: Oct 15, 2020Filed: Nov 24, 2021Published: Apr 21, 2022

Est. expiryOct 15, 2040(~14.2 yrs left)· nominal 20-yr term from priority

Inventors:Bassam El Ali Waseem Mansour Mohammed Fettouhi

C07C 17/278C07F 15/006C07D 307/77

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References

Claims

Abstract

This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.

Claims

exact text as granted — not AI-modified

What is claimed is: 
     
         1 . A compound of Formula (I): 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  and R 2  are each independently selected from C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, aryl, 5-7 membered heteroaryl, 5-7 membered heterocycloalkyl, (C 1 -C 3  alkylene)-(C 3 -C 10  cycloalkyl), (C 1 -C 3  alkylene)-aryl, (C 1 -C 3  alkylene)-(5-7 membered heteroaryl), and (C 1 -C 3  alkylene)-(5-7 membered heterocycloalkyl), wherein the alkyl is optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —NH 2 , C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 3 -C 6  cycloalkyl, —O—(C 1 -C 3  alkyl), (C 1 -C 3  alkylene)-O—(C 1 -C 3  alkyl), and aryl; 
 X is selected from Cl, Br, and I; and 
 n is 1 to 4. 
 
     
     
         2 . The compound of  claim 1 , wherein R 1  and R 2  are each independently C 1 -C 6  alkyl optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —NH 2 , C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 3 -C 6  cycloalkyl, —O—(C 1 -C 3  alkyl), (C 1 -C 3  alkylene)-O—(C 1 -C 3  alkyl), and aryl. 
     
     
         3 . The compound of  claim 3 , wherein R 1  and R 2  are each independently selected from methyl, ethyl, propyl, isopropyl, and butyl. 
     
     
         4 . The compound of  claim 3 , wherein R 1  and R 2  are each isopropyl. 
     
     
         5 . The compound of  claim 1 , wherein X is Br. 
     
     
         6 . The compound of  claim 1 , wherein n is 1, 2, or 3. 
     
     
         7 . The compound of  claim 1 , wherein:
 R 1  and R 2  are each independently selected from C 1 -C 6  alkyl optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —NH 2 , C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 3 -C 6  cycloalkyl, —O—(C 1 -C 3  alkyl), (C 1 -C 3  alkylene)-O—(C 1 -C 3  alkyl), and aryl;   X is selected from Cl, Br, and I; and   n is 1, 2, or 3.   
     
     
         8 . The compound of  claim 7 , wherein R 1  and R 2  are each independently selected from methyl, ethyl, propyl, isopropyl, and butyl. 
     
     
         9 . The compound of  claim 8 , wherein R 1  and R 2  are each isopropyl. 
     
     
         10 . The compound of  claim 7 , wherein X is Br. 
     
     
         11 . The compound of  claim 7 , wherein n is 1. 
     
     
         12 . The compound of  claim 7 , wherein n is 2. 
     
     
         13 . The compound of  claim 7 , wherein n is 3. 
     
     
         14 . The compound of  claim 1 , wherein the compound of Formula (I) is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         15 . A method of preparing a compound of Formula (I) according to  claim 1 , the method comprising contacting a compound of Formula (II) with a palladium catalyst to form a compound of Formula (I), wherein the compound of Formula (II) has the structure: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  and R 2  are each independently selected from C 1 -C 10  alkyl, C 1 -C 10  haloalkyl, C 3 -C 10  cycloalkyl, aryl, 5-7 membered heteroaryl, 5-7 membered heterocycloalkyl, (C 1 -C 3  alkylene)-(C 3 -C 10  cycloalkyl), (C 1 -C 3  alkylene)-aryl, (C 1 -C 3  alkylene)-(5-7 membered heteroaryl), and (C 1 -C 3  alkylene)-(5-7 membered heterocycloalkyl), wherein the alkyl is optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —NH 2 , C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 3 -C 6  cycloalkyl, —O—(C 1 -C 3  alkyl), (C 1 -C 3  alkylene)-O—(C 1 -C 3  alkyl), and aryl; 
 X is selected from Cl, Br, and I; and 
 n is 1 to 4. 
 
     
     
         16 . The method of  claim 15 , wherein R 1  and R 2  are each independently C 1 -C 6  alkyl optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —NH 2 , C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 3 -C 6  cycloalkyl, —O—(C 1 -C 3  alkyl), (C 1 -C 3  alkylene)-O—(C 1 -C 3  alkyl), and aryl. 
     
     
         17 . The method of  claim 15 , wherein R 1  and R 2  are each independently selected from methyl, ethyl, propyl, isopropyl, and butyl. 
     
     
         18 . The method of  claim 17 , wherein R 1  and R 2  are each isopropyl. 
     
     
         19 . The method of  claim 15 , wherein X is Br. 
     
     
         20 . The method of  claim 15 , wherein n is 1. 
     
     
         21 . The method of  claim 15 , wherein n is 2. 
     
     
         22 . The method of  claim 15 , wherein n is 3. 
     
     
         23 . The method of  claim 15 , wherein the compound of Formula (II) is selected from:

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