CN101402536A - Process for producing compound with steric hindrance biaryl base - Google Patents
Process for producing compound with steric hindrance biaryl base Download PDFInfo
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- CN101402536A CN101402536A CNA2008102021242A CN200810202124A CN101402536A CN 101402536 A CN101402536 A CN 101402536A CN A2008102021242 A CNA2008102021242 A CN A2008102021242A CN 200810202124 A CN200810202124 A CN 200810202124A CN 101402536 A CN101402536 A CN 101402536A
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Abstract
The invention relates to a method for preparing a biaryl-based compound with steric hindrance, in particular to a method for preparing the biaryl-based compound with the steric hindrance through double Suzuki cross-coupling reaction, which belongs to the technical field of chemical preparation. The method comprises the following steps: dissolving dihalogenated aryl compound and palladium catalyst of which the molar ratio is between (100 to 1) and (10 to 1) in DMF, DME/H2O or DME/tBuOH, heating up the mixture to make the mixture into a homogeneous system, then dropping aryl boric acid and alkali into the homogeneous system in turn, reacting the mixture fully at a temperature between 60 DEG C and the boiling point, naturally cooling the mixture to room temperature, extracting the mixture, combining organic phase, washing and drying the mixture, rotatably evaporating the mixture to remove solvent, and finally performing column chromatography to separate the mixture to obtain the biaryl-based compound with the steric hindrance (I). The method prepares a series of biaryl-based compounds with the steric hindrance fast and efficiently by using high steric hindrance Suzuki cross-coupling reaction, and the compounds with the steric hindrance have wide application prospect in the aspects of medicine, liquid crystal materials, luminous elements and the like.
Description
Technical field
The present invention relates to a kind of preparation method with the steric hindrance biaryl base compound, is to utilize two Suzuki cross-coupling reactions to prepare the method for band steric hindrance biaryl base compound specifically, belongs to the chemical preparation technical field.
Background technology
Aryl-linking compound in medicine, liquid crystal material, luminescent device, have widely and to use (Chem.Rev, 2006,106,2651-2710).Its preparation is main by Suzuki coupling, Kharash coupling, Negishi coupling, Stille coupling, reactions such as Himaya coupling, Liebeskind-Srogl coupling, Kumuda coupling, Suzuki cross-coupling reaction, the productive rate advantages of higher low (Tetrahedron that is used widely wherein because of its reaction conditions gentleness, applicable multiple functional group, aryl boric acid toxicity, 2002,58,9633-9695).Reported that in patent CN101050157A a kind of Suzuki of utilization cross-coupling reaction prepares the method for biphenyl compound.Reported that in patent CN101182310A a kind of Suzuki of utilization cross-coupling reaction prepares the method for the pyridine compounds and their of xenyl replacement.
Suzuki cross-coupling reaction development in recent years is rapid, yet has all obtained bigger breakthrough in fundamental research and application facet., when reactant molecule had than the large space steric hindrance, reaction often was difficult to carry out.Especially when aryl boric acid has than the large space steric hindrance, owing to its space steric effect and the protonated deboration of easier generation make reaction difficulty more.Recently, high sterically hindered Suzuki cross-coupling reaction has also been obtained certain progress, as document (Inorganica Chimica Acta, 2006,359,1947-1954; Organometallics, 2005,24,353-357; J.Am.Chem.Soc.2005,127,4685-4696; Tetrahedron Lett.2001,42,6667-6670; Org.Lett.2005,7,3721-3724).Yet all there be catalyzer and the part of employing than complexity and non-commercialization in these reported method, and the reaction required time is longer, the low deficiency that waits of the higher or yield of temperature of reaction.Do not relate in the prior art as shown in the present at Pd (PPh
3)
4As catalyzer, KO
tUnder the condition of Bu as alkali, utilize the two Suzuki cross-coupling reactions of high steric hindrance to prepare the method for band steric hindrance biaryl base compound.
Summary of the invention
The object of the invention is, a kind of high efficiency method that makes things convenient for of the preparation band steric hindrance biaryl base compound that utilizes two Suzuki cross-coupling reactions is provided.
The band steric hindrance biaryl base compound of the present invention's preparation has structure shown in the general formula (I).
In the general formula (I):
R is selected from: H, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, itrile group or aldehyde radical.
Ar is selected from: phenyl, substituted-phenyl, thiophene, substituted thiophene, pyridine, substituted pyridines etc.
In the general formula (I), substituted-phenyl is selected from: C
1-C
6Alkyl-substituted phenyl, C
1-C
6Alkoxy substituted phenyl, itrile group phenyl, aldehyde radical phenyl, fluoro phenyl or chlorophenyl.
Substituted thiophene is selected from: C
1-C
6Alkylated substituted thiazoline fen, C
1-C
6Alkoxyl group substituted thiophene, cyano-thiophene, aldehyde radical thiophene, fluoro thiophene or chloro thiophene.
Substituted pyridines is selected from: C
1-C
6Alkyl substituted pyridines, C
1-C
6Alkoxyl group substituted pyridines, itrile group pyridine, aldehyde radical pyridine, fluorinated pyridine or chloro-pyridine.
The alkyl of indication comprises the straight or branched alkyl in general formula (I).Alkoxyl group comprises the straight or branched alkoxyl group.
The structural compounds preparation method is as follows shown in the formula of of the present invention (I):
Key step: with mol ratio is that the dihalo aryl compound and the palladium catalyst of (100: 1)～(10: 1) is dissolved in DMF, DME/H
2O or DME/
tAmong the BuOH, heating makes it become homogeneous system, aryl boric acid and the alkali that drips successively then, and wherein the mol ratio of aryl boric acid and dihalo aryl compound is (2～5): 1; Alkali is salt of wormwood, potassiumphosphate, hydrated barta, cesium carbonate or potassium tert.-butoxide, and with the mol ratio of dihalo aryl compound be (3～8): 1; 60 ℃ to fully reaction between the boiling point, naturally cool to room temperature, add entry (10mL) dilution, ethyl acetate (10mL * 3) extraction.Merge organic phase, use the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain being with steric hindrance biaryl base compound (I) at last.
Dihalo aryl compound among the preparation method of band steric hindrance biaryl base compound provided by the invention is two iodo aryl compounds or two bromo aryl compounds.
Employed palladium catalyst is Pd (PPh among the preparation method of band steric hindrance biaryl base compound provided by the invention
3)
4, the mol ratio of catalyst consumption and raw material is (100: 1)～(10: 1), optimum molar ratio is (100: 3)～(100: 6).
Employed solvent is DMF among the preparation method of band steric hindrance biaryl base compound provided by the invention, DME/H
2O or DME/
tBuOH, optimum solvent is DME/
tBuOH.
Employed alkali is salt of wormwood, potassiumphosphate, hydrated barta in the preparation of band steric hindrance biaryl base compound provided by the invention, and cesium carbonate or potassium tert.-butoxide, best alkali are potassium tert.-butoxide.
The present invention be simple and easy to and commercial catalyst P d (PPh
3)
4With highly basic KO
tUnder the Bu existence condition, utilize high steric hindrance Suzuki cross-coupling reaction quickness and high efficiency preparation a series of band steric hindrance biaryl base compounds, such aryl-linking compound has wide practical use at aspects such as medicine, liquid crystal material, luminescent devices.
Embodiment
The following example can be used to further specify the present invention, but does not mean that restriction the present invention.
Embodiment 1
1,4-diiodo-benzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 1 in the reaction flask of 50mL, and the 4-diiodo-benzene (0.33g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.30g at last, and yield is 96%.
Embodiment 2
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 1 in the reaction flask of 50mL, and the 4-dibromobenzene (0.24g, 1mmol), PdCl
2(PPh
3)
2(0.035g, 0.05mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.26g at last, and yield is 82%.
Embodiment 3
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 1 in the reaction flask of 50mL, and the 4-dibromobenzene (0.24g, 1mmol), Pd (OAc)
2(0.012g, 0.05mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.24g at last, and yield is 76%.
Embodiment 4
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 1 in the reaction flask of 50mL, and the 4-dibromobenzene (0.24g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.28g at last, and yield is 88%.
Embodiment 5
2,5-dibromomethylbenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 2 in the reaction flask of 50mL, and the 5-dibromomethylbenzene (0.25g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.30g at last, and yield is 91%.
Embodiment 6
2,5-dibromo p-Xylol and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 2 in the reaction flask of 50mL, and 5-dibromo p-Xylol (0.26g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.31g at last, and yield is 91%.
Embodiment 7
2,5-dibromobenzene formonitrile HCN and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 2 in the reaction flask of 50mL, and 5-dibromobenzene formonitrile HCN (0.26g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.20g at last, and yield is 58%.
Embodiment 8
4,4 '-dibromo biphenyl and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 4 in the reaction flask of 50mL, and 4 '-dibromo biphenyl (0.31g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.30g at last, and yield is 77%.
Embodiment 9
2,7-dibromo fluorenes and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 2 in the reaction flask of 50mL, and 7-dibromo fluorenes (0.32g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.16g at last, and yield is 40%.
Embodiment 10
2,5-dibromo thiophene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 2 in the reaction flask of 50mL, and the 5-dibromo thiophene (0.24g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.30g at last, and yield is 94%.
Embodiment 11
2,5-two bromo-3 methyl thiophenes and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 2 in the reaction flask of 50mL, and 5-two bromo-3 methyl thiophenes (0.26g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.26g at last, and yield is 77%.
Embodiment 12
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 1 in the reaction flask of 50mL, and the 4-dibromobenzene (0.24g, 1mmol), Pd (PPh
3)
4(0.012g, 0.01mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.66g, 4mmol) and be dissolved in
tThe KO of BuOH
tBu (0.78g, 7mmol).After the reflux 5 minutes, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.21g at last, and yield is 67%.
Embodiment 13
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, add 1 in the reaction flask of 50mL, and the 4-dibromobenzene (0.24g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), DME (8mL), heated and stirred makes it become homogeneous system.Slowly drip successively and be dissolved in 2,4 of DME (2mL), and 6-Three methyl Benzene boric acid (0.50g, 3mmol) and be dissolved in
tThe KO of BuOH
tBu (0.45g, 4mmol).After the reflux three hours, naturally cool to room temperature.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.23g at last, and yield is 72%.
Following example as a comparison
Embodiment 14
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, in the reaction flask of 50mL with 1, the 4-dibromobenzene (0.24g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), 2,4,6-Three methyl Benzene boric acid (0.50g, 4mmol), Cs
2CO
3(4mmol 1.3g) is dissolved among the DMF (10ml), and 80 ℃ of reactions naturally cooled to room temperature after 3 hours.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation to obtain white solid product 0.06g at last, and yield is 20%.
Embodiment 15
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, in the reaction flask of 50mL with 1, the 4-dibromobenzene (0.24g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), 2,4,6-Three methyl Benzene boric acid (0.50g, 4mmol), K
3PO
4(4mmol 0.95g) is dissolved among the DMF (10ml), and 80 ℃ of reactions naturally cooled to room temperature after 6 hours.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation only to obtain white solid product 0.015g at last, and yield is 5%.
Embodiment 16
1,4-dibromobenzene and 2,4, the linked reaction of 6-Three methyl Benzene boric acid
Under the nitrogen protection, in the reaction flask of 50mL with 1, the 4-dibromobenzene (0.24g, 1mmol), Pd (PPh
3)
4(0.07g, 0.06mmol), 2,4,6-Three methyl Benzene boric acid (0.50g, 4mmol), Ba (OH)
28H
2(4mmol 1.26g) is dissolved in DMF (10mL)/H to O
2Among the O (2mL), 80 ℃ of reactions naturally cooled to room temperature after 24 hours.Add entry (10mL) dilution, with ethyl acetate (10mL * 3) extraction.Merge organic phase, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and utilizes column chromatography for separation only to obtain white solid product 0.025g at last, and yield is 8%.
Claims (5)
1. preparation method with the steric hindrance biaryl base compound, employing be two Suzuki cross-coupling reactions, it is characterized in that: mol ratio is dissolved in DMF, DME/H for the dihalo aryl compound and the palladium catalyst of (100: 1)～(10: 1)
2O or DME/
tAmong the BuOH, heating makes it become homogeneous system, aryl boric acid and the alkali that drips successively then, and wherein the mol ratio of aryl boric acid and dihalo aryl compound is (2～5): 1; Alkali is salt of wormwood, potassiumphosphate, hydrated barta, cesium carbonate or potassium tert.-butoxide, and with the mol ratio of dihalo aryl compound be (3～8): 1; 60 ℃ between the boiling point fully the reaction, purifying must be with the steric hindrance biaryl base compound.
2. the preparation method of band steric hindrance biaryl base compound as claimed in claim 1 is characterized in that the dihalo aryl compound is two iodo aryl compounds or two bromo aryl compounds.
3. the preparation method of band steric hindrance biaryl base compound as claimed in claim 1 is characterized in that palladium catalyst is Pd (PPh
3)
4
4. the preparation method of band steric hindrance biaryl base compound as claimed in claim 1 is characterized in that solvent is DME/
tBuOH.
5. the preparation method of band steric hindrance biaryl base compound as claimed in claim 1 is characterized in that alkali is potassium tert.-butoxide.
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|---|---|---|---|
| CNA2008102021242A CN101402536A (en) | 2008-11-03 | 2008-11-03 | Process for producing compound with steric hindrance biaryl base |
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|---|---|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150031894A1 (en) * | 2011-12-27 | 2015-01-29 | Canon Kabushiki Kaisha | Novel organic compound |
| CN113831319A (en) * | 2021-10-19 | 2021-12-24 | 北京科技大学 | Suzuki reaction method of arylboronic acid/boric acid ester containing large steric hindrance substituent |
-
2008
- 2008-11-03 CN CNA2008102021242A patent/CN101402536A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150031894A1 (en) * | 2011-12-27 | 2015-01-29 | Canon Kabushiki Kaisha | Novel organic compound |
| US9284328B2 (en) * | 2011-12-27 | 2016-03-15 | Canon Kabushiki Kaisha | Organic compound |
| CN113831319A (en) * | 2021-10-19 | 2021-12-24 | 北京科技大学 | Suzuki reaction method of arylboronic acid/boric acid ester containing large steric hindrance substituent |
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