Catalyst

Patent metadata

Field	Value
Publication number	US-2016347906-A1
Application number	US-201515116678-A
Country	US
Kind code	A1
Filing date	Feb 6, 2015
Priority date	Feb 7, 2014
Publication date	Dec 1, 2016
Grant date	—

Abstract

The present invention provides novel catalysts of formula (I), where M 1 and M 2 are different and are independently selected from Mg, Zn, Fe, Co, Al and Cr, and catalyst systems comprising these catalysts. The invention also relates to the use of the inventive catalysts and catalyst systems to catalyse the reaction between i) carbon dioxide and an epoxide, ii) an epoxide and an anhydride, or iii) a lactide and/or a lactone. The invention also relates to a method for producing a catalyst of formula (I).

First claim

1 . A catalyst of formula (I):

wherein:
M 1 and M 2 are different and are independently selected from the group consisting of Mg, Zn, Fe, Co, Al, and Cr;
each instance of R 1 and R 2 is independently hydrogen, halide, a nitro group, a nitrile group, an imine, an amine, an ether group, a silyl group, a silyl ether group, a sulfoxide group, a sulfonyl group, a sulfinate group, an acetylide group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted haloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkylthio, optionally substituted arylthio, optionally substituted alicyclic, or optionally substituted heteroalicyclic;
each instance of R 3 is independently optionally substituted alkylene, optionally substituted alkenylene, optionally substituted alkynylene, optionally substituted heteroalkylene, optionally substituted heteroalkenylene, optionally substituted heteroalkynylene, optionally substituted arylene, optionally substituted heteroarylene or optionally substituted cycloalkylene, wherein the alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene and heteroalkynylene, may optionally be interrupted by optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alicyclic, or optionally substituted heteroalicyclic;
each instance of R 4 is independently H, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylheteroaryl or optionally substituted alkylaryl;
each instance of R 5 is independently H, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylheteroaryl, or optionally substituted alkylaryl;
E 1 is C and E 2 is O, S or NH, or E 1 is N and E 2 is O;
each instance of X is independently OC(O)R x , OSO 2 R x , OSOR x , OSO(R x ) 2 , S(O)R x , OR x , phosphinate, halide, nitrate, hydroxyl, carbonate, amino, amido, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted aryl, or optionally substituted heteroaryl;
each instance of R x is independently hydrogen, optionally substituted aliphatic, optionally substituted haloaliphatic, optionally substituted heteroaliphatic, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted aryl, optionally substituted alkylaryl, or optionally substituted heteroaryl; and
G is absent or independently a neutral or anionic donor ligand which is a Lewis base.

2 . The catalyst according to claim 1 , wherein M 1 and M 2 are independently selected from Mg, Zn, Fe and Co.

3 . The catalyst according to claim 1 , wherein M 1 is either Mg or Zn.

4 . The catalyst according to claim 1 , wherein M 1 is Zn and M 2 is Mg.

5 . The catalyst according to claim 1 , wherein each instance of R 2 , R 4 and R 5 is H, R 3 is an optionally substituted propylene, optionally substituted phenylene, or optionally substituted cyclohexylene, E 1 is C, and E 2 is O, S or NH.

6 . The catalyst according claim 1 , wherein each instance of R 1 is independently hydrogen, halide, amino, nitro, sulfoxide, sulfonyl, silyl, sulfinate, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, or optionally substituted alkylthio.

7 . The catalyst according to claim 1 , wherein each instance of X is independently OC(O)R x , OSO 2 R x , OS(O)R x , OSO(R x ) 2 , S(O)R x , OR x , halide, nitrate, hydroxyl, carbonate, amino, nitro, amido, optionally substituted alkyl, optionally substituted heteroalkyl, aryl, or optionally substituted heteroaryl.

8 . The catalyst according to claim 1 , wherein each instance of R x is independently optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted heteroalkyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted alkylaryl.

9 . The catalyst according to claim 1 having the formula:

10 . A catalyst system comprising a catalyst of claim 1 .

11 . The catalyst system according to claim 10 , further comprising a second catalyst or a co-catalyst.

12 . The catalyst system according to claim 11 , wherein the second catalyst is a compound of formula (Ic):

wherein:
M 1 and M 2 may be the same or different, and are selected from the group consisting of Zn(II), Cr(II), Co(II), Mn(II), Mg(II), Fe(II), Ti(II), Cr(III)-X, Co(III)-X, Mn(III)-X, Fe(III)-X, Ca(II), Ge(II), Al(III)-X, Ti(III)-X, V(III)-X, Ge(IV)-(X) 2 and Ti(IV)-(X) 2 ;
each instance of R 1 and R 2 is independently hydrogen, halide, a nitro group, a nitrile group, an imine, an amine, an ether group, a silyl group, a silyl ether group, a sulfoxide group, a sulfonyl group, a sulfinate group, an acetylide group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted haloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkylthio, optionally substituted arylthio, optionally substituted alicyclic, or optionally substituted heteroalicyclic;
each instance of R 3 is independently optionally substituted alkylene, optionally substituted alkenylene, optionally substituted alkynylene, optionally substituted heteroalkylene, optionally substituted heteroalkenylene, optionally substituted heteroalkynylene, optionally substituted arylene, optionally substituted heteroarylene or optionally substituted cycloalkylene, wherein the alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene and heteroalkynylene, may optionally be interrupted by optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alicyclic, or optionally substituted heteroalicyclic;
each instance of R 4 is independently H, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylheteroaryl or optionally substituted alkylaryl;
each instance of R 5 is independently H, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylheteroaryl, or optionally substituted alkylaryl;
E 1 is C and E 2 is O, S or NH, or E 1 is N and E 2 is O;
each instance of X is independently OC(O)R x , OSO 2 R x , OSOR x , OSO(R x ) 2 , S(O)R x , OR x , phosphinate, halide, n

Assignees

• Imp Innovations Ltd

Inventors

• Williams Charlotte
• Saini Prabhjot
• Romain Charles
• Garden Jennifer

Classifications

• B01J2531/22

  Magnesium · CPC title

• B01J2531/0241

  Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution · CPC title

• B01J2531/26

  Zinc · CPC title

• C07F15/065

  without a metal-carbon linkage · CPC title

• B01J31/2243 Primary

  At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand · CPC title