# US 8,785,665 B2 · Surfactant-enabled transition metal-catalyzed chemistry

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- Number: US 8,785,665 B2
- Document ID: US8785665B2
- Status: Granted
- Kind: B2
- Application number: 12/958,288
- Filed: 2010-12-01
- Published: 2011-06-02
- Granted: 2014-07-22
- Earliest claimed: 2009-12-01
- Assignees: MyCell Technologies, LLC
- Applicants: Volker Berl
- Inventors: Volker Berl
- Web page: https://patentgrep.com/patent/US8785665B2

## CPC

- C07D 311/72: 3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
- B01J 31/068: {Polyalkylene glycols}
- B01J 31/2226: {Anionic ligands, i.e. the overall ligand carries at least one formal negative charge}
- B01J 31/2278: {Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts}
- B01J 31/24: Phosphines {, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands}
- C07C 1/321: {the hetero-atom being a non-metal atom}
- C07C 2/861: {the non-hydrocarbon contains only halogen as hetero-atoms}
- C07C 17/263: by condensation reactions
- C07C 41/30: by increasing the number of carbon atoms, e.g. by oligomerisation
- C07C 67/343: by increase in the number of carbon atoms
- C07C 209/10: with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
- C07C 209/16: with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C 209/18: with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
- C07C 227/18: by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
- C07C 231/12: by reactions not involving the formation of carboxamide groups
- C07C 253/30: by reactions not involving the formation of cyano groups
- C07C 273/1854: {by reactions not involving the formation of the N-C(O)-N- moiety}
- C07D 211/94: Oxygen atom, e.g. piperidine N-oxide
- C07D 211/96: Sulfur atom
- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 223/04: with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 249/06: with aryl radicals directly attached to ring atoms
- C07F 7/1892: {by reactions not provided for in C07F7/1876 - C07F7/1888}
- B01J 2231/323: Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
- B01J 2231/4211: Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
- B01J 2231/4261: Heck-type, i.e. RY + C=C, in which R is aryl
- B01J 2231/4266: Sonogashira-type, i.e. RY + HC-CR' triple bonds, in which R=aryl, alkenyl, alkyl and R'=H, alkyl or aryl
- B01J 2231/4283: using N nucleophiles, e.g. Buchwald-Hartwig amination
- B01J 2231/44: Allylic alkylation, amination, alkoxylation or analogues
- B01J 2231/543: alkene metathesis
- B01J 2531/824: Palladium
- C07C 2531/24: Phosphines
- C07C 2601/16: the ring being unsaturated
- C07C 2603/74: Adamantanes
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.

## Claims

### Claim 1

A mixture comprising
(a) water in an amount of at least 1% wt/wt of the mixture;
(b) a transition metal catalyst; and
(c) a solubilizing agent having the formula
Y1-L1-z
wherein Z is a hydrophobic group,
and Y1-L1- has the formula:
wherein n is an integer selected from 2-10,
k is 16-20, and Y7 is methyl.

### Claim 2 (depends on 1)

The mixture of claim 1, wherein the transition metal catalyst is selected from an organo-palladium or -nickel reagent, organo-copper or -gold reagent, organo-rhodium or -iridium complex, or an organo-ruthenium, -iron, or -osmium reagent, wherein the catalyst is capable of promoting cross-coupling reactions, or other reactions characteristic of catalysis by these metals, that form a carbon-carbon, carbon-heteroatom or carbon-hydrogen bond.

### Claim 3 (depends on 1)

The mixture of claim 1, wherein the transition metal catalyst comprises less than 5 mole %, less than 3 mole % or less than2 mole % of the mixture.

### Claim 4 (depends on 1)

The mixture of claim 1, further comprising (i) a coupling substrate and (ii) a coupling partner.

### Claim 5 (depends on 4)

The mixture of claim 4, wherein water is the sole solvent.

### Claim 6 (depends on 5)

The mixture of claim 5, wherein the coupling substrate is selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; and wherein the coupling partner is selected from H, substituted or unsubstituted amine, substituted or unsubstituted silane, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

### Claim 7 (depends on 4)

The mixture of claim 4, wherein the coupling substrate is a substituted or unsubstituted alkene, a substituted or unsubstituted alkyne, a substituted or unsubstituted enyne, a substituted or unsubstituted enone or enoate or a substituted or unsubstituted ynone or ynoate.

### Claim 8 (depends on 4)

The mixture of claim 4, wherein the coupling substrate is selected from a substituted or unsubstituted vinyl halide, substituted or unsubstituted vinyl pseudohalide, substituted or unsubstituted allylic alcohol, substituted or unsubstituted allylic ether, substituted or unsubstituted aryl or heteroaryl halide and substituted or unsubstituted aryl or heteroaryl pseudohalide.

### Claim 9 (depends on 4)

The mixture of claim 4, wherein the coupling partner is selected from a mono-substituted, disubstituted, trisubstituted, or tetrasubstituted alkene, mono-substituted or disubstituted alkyne, substituted or unsubstituted aryl or heteroaryl halide and substituted or unsubstituted aryl or heteroaryl pseudohalide.

### Claim 10 (depends on 4)

The mixture of claim 4, wherein the mixture provides a medium for transition metal-catalyzed cross-coupling reaction comprising olefin cross-metathesis, ring closing metathesis, Sonogashira coupling, Heck coupling, direct amination of free allylic alcohols, aminations of allylic ethers, C—H activation reactions, Suzuki-Miyaura coupling, Buchwald-Hartwig amination, Negishi couplings, benzylic couplings with aryl halides or pseudohalides, silylations of allylic ethers, and aryl-aryl cross-couplings.

### Claim 11 (depends on 10)

The mixture of claim 10, wherein the reaction is accelerated by increasing the ionic strength of the reaction medium and/or by the reduction of the pH of the reaction mixture.

### Claim 12 (depends on 11)

The mixture of claim 11, wherein increasing the ionic strength is performed by the addition of a metal salt or mixtures of salts, and/or the pH is reduced to a range of pH 2-6.

### Claim 13 (depends on 1)

The mixture of claim 1, wherein the hydrophobic group is selected from the group consisting of natural or synthetic alpha-tocopherol, and a ubiquinol moiety.

### Claim 14 (depends on 1)

The mixture of claim 1, wherein the hydrophobic group is selected from the group consisting of α-, β-, γ- and Δ-tocopherol.

### Claim 15 (depends on 14)

The mixture of claim 14, wherein the hydrophobic group is selected from the group consisting of α-(+)-tocopherol and α-(±)-tocopherol.