Phosphine ligands for catalytic reactions

Patent metadata

Field	Value
Publication number	US-2016263566-A1
Application number	US-201615164002-A
Country	US
Kind code	A1
Filing date	May 25, 2016
Priority date	Jul 16, 2010
Publication date	Sep 15, 2016
Grant date	—

Abstract

The disclosure is directed to: (a) phosphacycle ligands; (b) catalyst compositions comprising phosphacycle ligands; and (c) methods of using such phosphacycle ligands and catalyst compositions in bond forming reactions.

First claim

1 - 30 . (canceled)

31 . A compound having a structure corresponding to formula (I), or a salt thereof,

wherein Ar 1 and Ar 2 are each independently aryl or heteroaryl, and wherein Ar 1 and Ar 2 are each independently optionally substituted with one or more R 1 and R 2 , respectively;
R 1 and R 2 are independently selected at each occurrence from the group consisting of hydrogen; amino; hydroxyl; cyano; halo; alkyl; alkenyl; alkynyl; haloalkyl; haloalkoxy; oxoalkyl; alkoxy; aryloxy; heteroaryloxy; arylamino; heteroarylamino; alkylamino; dialkylamino; cycloalkyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; cycloalkyloxy optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; 5- or 6-membered heteroaryl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; phenyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; hydroxyalkyl; hydroxyalkoxy; alkoxyalkyl; aminoalkyl; N-alkylaminoalkyl; N,N-dialkylaminoalkyl; N,N,N-trialkylammoniumalkyl; L 1 -C(O)—OR 1′ , L 1 -P(O)—(OR 1′ ) 2 , or L 1 -S(O) 2 —OR 1′ , wherein L 1 is a bond or alkylene, and R 1′ is selected from the group consisting of hydrogen, alkyl and hydroxyalkyl; L 2 -O—C(O)—R 2′ , wherein L 2 is a bond or alkylene, and R 2′ is alkyl or hydroxyalkyl; L 3 -C(O)—NR 3′ R 4′ , wherein L 3 is a bond or alkylene, and R 3′ and R 4′ are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl; L 4 -NR 5′ —C(O)—R 6′ , wherein L 4 is a bond or alkylene, R 5′ is hydrogen or alkyl, and R 6′ is alkyl or hydroxyalkyl; sulfamoyl; N-(alkyl)sulfamoyl; N,N-(dialkyl)sulfamoyl; sulfonamide; sulfate; alkylthio; thioalkyl; and a ring containing an alkylene or —O—(CH 2 ) m —O— formed by the joining together of any two R 1 or any two R 2 or an R 1 and an R 2 , wherein m is 1, 2, 3 or 4;
X is a phosphine of formula (Ia):

wherein ring A includes 0 to 9 ring atoms in addition to the phosphorus and 2 carbon ring atoms of formula (Ia), wherein said ring atoms are each independently selected from the group consisting of carbon, oxygen, nitrogen, phosphorus and sulfur; and
wherein the ring atoms of ring A are each independently optionally substituted with one or more substituents selected from the group consisting of alkenyl; alkoxy; alkoxyalkyl; alkyl; alkylamino; alkylthio; alkynyl; aminoalkyl; N-alkylaminoalkyl; N,N-dialkylaminoalkyl; N,N,N-trialkylammoniumalkyl; arylalkyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; cycloalkyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; dialkylamino; halo; haloalkyl; fluoroalkyl; heteroaryl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; heterocycloalkyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; hydroxy; hydroxyalkyl; oxo; an exocyclic double bond optionally substituted with alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocyclyl, or heteroaryl; a 3- to 7-membered spiro ring containing zero, one, or two heteroatoms; phenyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; L 1 -C(O)—OR 1′ , L 1 -P(O)—(OR 1′ ) 2 , or L 1 -S(O) 2 —OR 1′ , wherein L 1 is a bond or alkylene, and R 1′ is selected from the group consisting of hydrogen, alkyl or hydroxyalkyl; L 2 -O—C(O)—R 2′ , wherein L 2 is a bond or alkylene, and R 2′ is alkyl or hydroxyalkyl; L 3 -C(O)—NR 3′ R 4′ , wherein L 3 is a bond or alkylene, and R 3′ and R 4′ are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl; L 4 -NR 5′ —C(O)—R 6′ , wherein L 4 is a bond or alkylene, R 5′ is hydrogen or alkyl, and R 6′ is alkyl or hydroxyalkyl; and L 7 -NR 8′ —S(O) 2 —R 9′ , wherein L 7 is a bond or alkylene, R 8′ is hydrogen or alkyl, and R 9′ is alkyl or hydroxyalkyl; and
as to R 10 , R 11 , R 12 , and R 13 ,
i. R 10 or R 11 together with R 12 or R 13 form a ring; or
ii. R 10 and R 11 together with the carbon atom to which they are attached form a spirocyclic ring and/or R 12 and R 13 together with the carbon atom to which they are attached form a spirocyclic ring;
wherein, any of substituents R 10 , R 11 , R 12 , and R 13 that do not form the ring set forth in (i) or (ii) are each independently selected from the group consisting of hydrogen; alkyl; alkenyl; haloalkyl; alkynyl; oxoalkyl; cycloalkyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; heterocyclyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; heteroaryl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; phenyl optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, cyano, halo, haloalkyl or haloalkoxy; hydroxyalkyl; alkoxyalkyl; aminoalkyl; N-alkylaminoalkyl; N,N-dialkylaminoalkyl; N,N,N-trialkylammoniumalkyl; thioalkyl; L 13 -C(O)—OR 14′ , L 13 -P(O)—(OR 14′ ) 2 , or L 13 -S(O) 2 —OR 14′ , wherein L 13 is a bond or alkylene, and R 14′ is selected from the group consisting of hydrogen, alkyl and hydroxyalkyl; L 15 -O—C(O)—R 16′ , wherein L 15 is alkylene and R 16′ is alkyl or hydroxyalkyl; L 17 -C(O)—NR 18′ R 19′ , wherein L 17 is a bond or alkylene, and R 18′ and R 19′ are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl; and L 2 -NR 2′ —C(O)—R 22′ , wherein L 20 is alkylene, R 21′ is hydrogen or alkyl, and R 22′ is alkyl or hydroxyalkyl.

32 . The compound or salt of claim 31 , wherein the compound has a structure corresponding to a structure of a formula selected from the group consisting of formulae (I-1) -(I-42):

wherein
V 1 , V 2 , V 3 , and V 4 are each independently CR 1 or N;
V 5 , V 6 , V 7 , V 8 and V 9 are each independently CR 2 or N;
W 1 , W 2 , an W 3 are each independently selected from the group consisting of CR 1 , NR 1 , N and O;
W 4 is C or N;
W 5 is C or N;
W 6 , W 7 , We and W 9 are each independently selected from the group consisting of CR 2 , NR 2 , N and O; and
ring C, at each occurrence, is a fused-aryl or fused-heteroaryl and is optionally substituted with R 1 and R 2 .

33 . The compound or salt of claim 31 , wherein the X is attached to an atom of Ar 1 adjacent to the atom bonded to Ar 2 .

34 . The compound or salt of claim 31 , wherein Ar 1 and Ar 2 are each aryl.

35 . The compound or salt of claim 31 , wherein Ar 2 is substituted with three R 2 .

36 . The compound or salt of claim 31 , wherein R 2 is alkyl.

37 . The compound or salt of claim 31 , wherein R 2 is isopropyl.

Assignees

• Abbvie Inc

Inventors

• Shekhar Shashank
• Franczyk Thaddeus S
• Barnes David M
• Dunn Travis B
• Haight Anthony R
• Chan Vincent S

Classifications

• C07C41/01

  Preparation of ethers · CPC title

• C07F9/657163

  the ring phosphorus atom being bound to at least one carbon atom · CPC title

• C07C201/10

  by substitution of functional groups by nitro groups · CPC title

• C07D209/12

  Radicals substituted by oxygen atoms · CPC title

• C07C303/40

  by reactions not involving the formation of sulfonamide groups · CPC title