Methods for the synthesis of olefins and derivatives
US-2019152887-A1 · May 23, 2019 · US
Oxidative coupling of aryl boron reagents with SP3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis
US10364208B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10364208-B2 |
| Application number | US-201815861020-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jan 3, 2018 |
| Priority date | Jan 5, 2017 |
| Publication date | Jul 30, 2019 |
| Grant date | Jul 30, 2019 |
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Abstract
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Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.
First claim
Opening claim text (preview).
What is claimed is: 1. A method for decarboxylative carbonyl α-arylation, comprising: reacting a. an aryl coupling partner, b. a beta-carbonyl carboxylic acid, and c. a copper based catalyst the reaction taking place at room temperature, exposed to air, thereby creating a carbon-carbon bond. 2. The method of claim 1 , wherein said carboxylic acid is a malonic acid derivative. 3. The method of claim 1 , wherein said carboxylic acid is a malonate ester, monoethyl malonate, monobenzyl malonate, mono-1-chlorohexyl malonate, mono-4-NBoc-piperidyl malonate, mono-geranyl malonate, 3-(methyl(phenyl)amino)-3-oxopropanoic acid, 3-oxo-3-(phenylamino)propanoic acid, 3-oxo-3-(pyrrolidin-1-yl)propanoic acid, or 3-(methoxy(methyl)amino)-3-oxopropanoic acid. 4. The method of claim 1 , wherein said coupling partner is an arylboronic ester or heteroaryl boronic ester. 5. The method of claim 1 , wherein said coupling partner is 3-iodophenyl boronic neopentyl ester [B(neop)], (ArBO) 3 , ArB(OH) 2 , ArBpin, or ArBF 3 K. 6. The method of claim 1 , wherein said copper based catalyst is a Cu(I) salt. 7. The method of claim 1 , wherein said copper based catalyst is a Cu(II) salt. 8. The method of claim 1 , wherein said copper based catalyst is Cu(OTf) 2 , Cu(OAc) 2 , CuSO 4 , Cu(MeCN) 4 PF 6 , or CuI.
Assignees
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Classifications
- C07C67/32Primary
Decarboxylation · CPC title
Boronic and borinic acid compounds · CPC title
having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals · CPC title
Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title
having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title
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- What does patent US10364208B2 cover?
- Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.
- Who is the assignee on this patent?
- Univ Alberta
- What technology area does this patent fall under?
- Primary CPC classification C07C67/32. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Jul 30 2019 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).