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Monday, 27 March 2017

Selective Oxidation of Benzylic C–H Using Nanoscale Graphene Oxide as Highly Efficient Carbocatalyst: Direct Synthesis of Terephthalic Acid

 Abstract Image
Nanoscale graphene oxide sheets (NGO), as activated carbocatalysts, were synthesized by a reduction size strategy and used in chemoselective oxidative conversion of benzylic C–H to the corresponding carboxylic acid. On the basis of the results of the optimization process of different parameters, 3 equiv of H2O2 for each C–H group, 100 wt % of NGO in aqueous medium, acetone as a cosolvent, and a reaction temperature of 100 °C were selected as optimum parameters.
In this optimum condition, xylenes and toluene over 24 h with good yield were converted to the corresponding carboxylic acid, and in the case of diphenylmethane and ethylbenzene, these substrates with excellent yield were converted to benzophenone and acetophenone.

Selective Oxidation of Benzylic C–H Using Nanoscale Graphene Oxide as Highly Efficient Carbocatalyst: Direct Synthesis of Terephthalic Acid

Institute of Industrial Chemistry, Iranian Research Organization for Science and Technology (IROST), P.O. Box 33535-111, Tehran, Iran
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.7b00056
 
*Tel.: +98 21 56276031. E-mail address: sedrpoushan1395@gmail.com (Alireza Sedrpoushan).
 
str1 str2 str3
///////

Thursday, 23 March 2017

A Brønsted acid catalysed enantioselective Biginelli reaction


A Bronsted acid catalysed enantioselective Biginelli reaction

Green Chem., 2017, 19,1529-1535
DOI: 10.1039/C6GC03274E, Paper
Margherita Barbero, Silvano Cadamuro, Stefano Dughera
A chiral derivative of 1,2-benzenedisulfonimide, namely (-)-4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Biginelli reaction.
 

A Brønsted acid catalysed enantioselective Biginelli reaction

*Corresponding authors
aDipartimento di Chimica, Università di Torino, C.so Massimo d'Azeglio 48, 10125 Torino, Italy
E-mail: stefano.dughera@unito.it
Green Chem., 2017,19, 1529-1535
A chiral derivative of 1,2-benzenedisulfonimide, namely (−)-4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Biginelli reaction. In fact the yields of the target dihydropyrimidines were very high (25 examples; average 91%) and enantiomeric excesses were always excellent (14 examples; average 97%). Ultimately, we herein propose a procedure that displays a number of benefits and advantages including the total absence of solvents, mild reaction conditions, relatively short reaction times and stoichiometric reagent ratios. Target dihydropyrimidines are obtained in adequate purity, making further chromatographic purification unnecessary. Moreover, the chiral catalyst was easily recovered from the reaction mixture and reused, without the loss of catalytic activity.
 
dihydropyrimidine-2-thiones 5
(R)-(-)-Ethyl 6-methyl-4-phenyl-2-thioxo-3,4-dihydropyrimidine-5-carboxylate (5a): pale grey solid (135 mg, 98% yield); mp 201–202 °C ( from EtOH; lit17 200–202 °C). 96.4% Ee (GC connected to a J&W Scientific Cyclosil-B column; stationary phase: 30% heptakis (2,3-di-Omethyl-6-O-t-butyldimethylsilyl)-β-cyclodextrin in DB-1701), tR= 12.11 min (major), tR= 12.54 min (minor); [a]D -65.4 (c 0.1 in MeOH). 1H NMR (200 MHz, DMSO-d6): δ = 10.24 (br s, 1H), 9.55 (br s, 1H), 7.31–7.12 (m, 5H), 5.09 (d, J = 3.9 Hz, 1H), 3.92 (q, J = 7.0 Hz, 2H), 2.21 (s, 3H), 1.01 (t, J = 7.0 Hz, 3H); 13C NMR (50 MHz, DMSO-d6): δ = 174.9, 165.8, 145.7, 129.3, 128.3, 127.0, 101.3, 60.2, 54.7, 17.8, 14.7. MS (m/z, EI): 276 [M+ ] (45), 247 (40), 199 (100). IR (neat) ν (cm−1): 3311 (NH), 3112 (NH), 1665 (CO), 1195 (CS).
 
 
 
Image result for Stefano Dughera

Dughera Dott. Stefano

Tel: 0116707645
Email: stefano.dughera@unito.it
address: Department of Chemistry
Dipartimento di Chimica, Università di Torino, C.so Massimo d'Azeglio 48, 10125 Torino, Italy
R. Fu, Y. Yang, W. Lai, Y. Ma, Z. Chen, J. Zhou, W. Chai, Q. Wang, and R. Yuan, Synth. Comm., 2015, 45, 477.
 
//////////////Brønsted acid,  catalysed,  enantioselective,  Biginelli reaction, dihydropyrimidine-2-thiones

Wednesday, 22 March 2017

5-chloro-6-morpholinonicotinic acid

Preparation of 5-chloro-6-morpholinonicotinic acid (18)1
A solution of ethyl 5,6-dichloronicotinate (A-1, 1.1 g, 5.0 mmol), N,N-diisopropylethylamine (DIPEA, 0.97
g, 7.5 mmol) in acetonitrile (3.0 mL) was treated with morpholine (0.48 g, 6.0 mmol). The mixture was
stirred for 6 hours at 95 °C. The complete conversion of the starting material could be detected by
observing a change of the color from yellowish to deep orange. After complete conversion, the mixture was
evaporated to dryness, the residue diluted with water (20 mL), and extracted with dichloromethane (3x20
mL). The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure to
yield 1.31 g (97 %) of A-2 as a red oil. The product was identified by LC/ESI-MS analysis and used for the
next synthetic step without further purification.
The ester A-2 (1.31 g, 4.83 mmol) was dissolved in a tetrahydrofurane/water mixture (1:1, 4.0 mL) and
treated with 2.0 M sodium hydroxide (0.33 g, 5.80 mmol). The reaction mixture was stirred for 5 h at 55 °C.
After complete conversion, the mixture was cooled to room temperature, diluted with water (20 mL) and
extracted with ethyl acetate (3x20 mL). The water layer was neutralized with an aqueous solution of
hydrochloric acid (2.0 N) until a white precipitate was observed. The product was collected by repeated
filtration and evaporation. The combined product fractions were dried at 70 °C yielding 1.17 g (100 %) of
18 as a white solid,
m.p. 185.2–186.2;
1H NMR (500 MHz, DMSO-d6) δ (ppm) 3.45 (t, J = 5.04 Hz, 2xCH2,4H), 3.72 (t, J = 4.41 Hz, 2xCH2, 4H), 8.08 (d, J = 1.89 Hz, CH, 1H), 8.66 (d, J = 1.90 Hz, CH, 1H), 13.01(s, CO2H, 1H). 13C (125 MHz, DMSO-d6) δ (ppm) 48.9 (2xCH2), 66.1 (2xCH2), 119.4, 139.7, 147.5, 159.3,
165.4;
LC/ESI-MS (m/z): 243.28 [M+H]+; Purity: 100.0 % (N).
Colandrea, V. J.; Doherty, G. A; Hale, J. J.; Huo, P.; Legiec, I. E.; Toth, L.; Vachal, P.; Yan, L. (3,4-
Disubstituted)propanoic carboxylates as S1P (EDG) receptor agonists. PCT Int. Appl. WO2005058848A1, 2005 (Merck & Co., Inc.).

Supporting Information

https://s3-eu-west-1.amazonaws.com/pstorage-acs-6854636/.../jm500729a_si_001.pdf

Tuesday, 21 March 2017

2-{[6-Chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]methyl}-4-fluorobenzonitrile

2-{[6-Chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]methyl}-4-fluorobenzonitrile (4)
white solid . Mp: 193–195 °C.
 
1H NMR (400 MHz, CDCl3) δ (ppm): 7.74–7.76(m, 1H), 7.14–7.17 (m, 1H), 6.95–6.97 (m, 1H), 6.05 (s, 1H), 5.51 (s, 2H), 3.40 (s, 3H).

2-({3-Methyl-6-[(3R)-3-piperidinylamino]-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)-4-fluorobenzonitrile

 

Figure
2-({3-Methyl-6-[(3R)-3-piperidinylamino]-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)-4-fluorobenzonitrile (8)
Mp: 90 °C decomposed.
 
1H NMR (400 MHz, CD3OD) δ (ppm): 7.85–7.89 (m, 1H), 7.25–7.28 (m, 1H), 6.96–6.99 (m, 1H), 5.37–5.51 (m, 2H), 4.84 (s, 1H), 3.42–3.49 (m, 1H), 3.28 (s, 3H), 3.11–3.15 (m, 1H), 2.89–2.93 (m, 1H), 2.46–2.58 (m, 2H), 1.92–1.95 (m, 1H), 1.48–1.70 (m, 3H).
 
MS (ESI+): m/z, 358.06 ([M + H]+).

Synthesis of 5,5'-[oxybis(methylene)]bis[2-furancarboxylic acid]


Graphical abstract: A two-step efficient preparation of a renewable dicarboxylic acid monomer 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid] from d-fructose and its application in polyester synthesis

A two-step efficient preparation of a renewable dicarboxylic acid monomer 5,5[prime or minute]-[oxybis(methylene)]bis[2-furancarboxylic acid] from D-fructose and its application in polyester synthesis

 
Green Chem., 2017, 19,1570-1575
DOI: 10.1039/C6GC03314H, Paper
Ananda S. Amarasekara, Loc H. Nguyen, Nnaemeka C. Okorie, Saad M. Jamal
A renewable monomer 5,5[prime or minute]-[oxybis(methylene)]bis[2-furancarboxylic acid] from D-fructose.

A two-step efficient preparation of a renewable dicarboxylic acid monomer 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid] from D-fructose and its application in polyester synthesis

*Corresponding authors
aDepartment of Chemistry, Prairie View A&M University, Prairie View, USA
E-mail: asamarasekara@pvamu.edu
Fax: +1 936 261 3117
Tel: +1 936 261 3107
Green Chem., 2017,19, 1570-1575
D-Fructose was converted to the dialdehyde 5,5′-[oxybis(methylene)]bis[2-furaldehyde] by heating at 110 °C in DMSO with the Dowex 50 W X8 solid acid catalyst in 76% yield without the isolation of the intermediate 5-hydroxymethylfurfural. This dialdehyde was then converted to the dicarboxylic acid monomer, 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid], using oxygen (1 atm.) and 5% Pt/C catalyst in 1.5 M aqueous NaOH at room temperature in 98% yield. The new dicarboxylic acid monomer can be considered as a renewable resource based alternative to terephthalic acid as demonstrated by the preparation of polyesters with 1,2-ethanediol and 1,4-butanediol in 87–92% yield.
 

Synthesis of 5,5'-[oxybis(methylene)]bis[2-furancarboxylic acid]

 
pale yellow crystals. 260 mg, 98 % yield. M.pt. 207-209 °C, Lit. M. pt. 209-210 °C 37 .
 
IR (ATR) 761, 891, 951, 1029, 1059, 1159, 1208, 1283, 1342, 1424, 1525, 1674, 3128 cm-1
 
1 H NMR (DMSO-d6 ) δ 3.38 (2H, bs, 2XCOOH), 4.51 (4H, s, 2X-CH2O ), 6.61 (2H, d, J = 3.6 Hz, C-4,4'), 7.15 (2H, d, J = 3.6 Hz, C-3,3').
 
13C NMR (DMSO-d6 ) δ 63.8, 112.2, 118.8, 145.3, 155.5, 159.6
37. T. Iseki and T. Sugiura, J. Biochem., 1939, 30, 113-118.
 
NMR PREDICT
1H NMR PREDICT
 
 
 
13C NMR PREDICT
 
 
//////////////O=C(O)c2ccc(COCc1ccc(o1)C(=O)O)o2
Nowruz 2017
Nowruz 2017

5,6-dihydropteridin-7(8H)-one

5,6-dihydropteridin-7(8H)-one
 
Org. Process Res. Dev.201721 (1), pp 11–17
DOI: 10.1021/acs.oprd.6b00219
/////////////

Monday, 20 March 2017

Regioselective access of alkylidendibenzo[c,f]oxocine framework via cyclocarbopalladation/cross-coupling cascade reactions and reductive Heck strategy

Regioselective access of alkylidendibenzo[c,f]oxocine framework via cyclocarbopalladation/cross-coupling cascade reactions and reductive Heck strategy

New J. Chem., 2017, Advance Article
DOI: 10.1039/C6NJ03825E, Paper
a
Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
E-mail: tapas.ghosh@uni-wuerzburg.de,tapasghosh.chem@gmail.com
Tel: +49-931-31-81629
New J. Chem., 2017, Advance Article
DOI: 10.1039/C6NJ03825E
Palladium-catalyzed dual strategies of cascade cyclocarbopalladation/cross-coupling of alkynes and a reductive Heck reaction have been developed to construct dibenzo[c,f]oxocine frameworks with tri- and tetra-substituted exo-cyclic alkenes with high stereo- and regio-control.
Palladium-catalyzed dual strategies of cascade cyclocarbopalladation/cross-coupling of alkynes and a reductive Heck reaction have been developed to construct dibenzo[c,f]oxocine frameworks with tri- and tetra-substituted exo-cyclic alkenes with high stereo- and regio-control. The success of this efficient methodology has been demonstrated by the synthesis of a number of dibenzoxocines in moderate to good yields and in sufficient quantities to support their further development.
 
 
12-benzylidene-7,12-dihydro-5H-dibenzo[c,f]oxocine (8a): The material obtained after workup was subjected to column chromatography on silica gel with petroleum ether/EtOAc (19:1) as eluent to deliver pure 8a. Off white solid, yield = 82%,
 
mp. 134-136 oC,
 
IR (KBr): 2861, 1623, 1602 cm-1 , 1H NMR (400 MHz, CDCl3): δH = 7.47 (d, 1H, J = 7.2 Hz), 7.19-7.34 (m, 5H), 7.05-7.15 (m, 5H), 6.94-6.96 (m, 2H), 6.64 (s, 1H), 4.87 (s, 2H), 4.75 (s, 2H).
 
13C NMR (100 MHz, CDCl3): δC = 144.6, 142.1, 138.3, 137.4, 136.9, 129.9, 129.1, 128.9, 128.6, 128.3, 128.1, 127.9, 127.4, 127.0, 126.7, 73.0, 70.3.
 
HRMS (ESI [M+Na]+ ): for C22H18O calcd 321.1255; found 321.1245.
 
 
 
///////Regioselective, alkylidendibenzo[c,f]oxocine, cyclocarbopalladation/cross-coupling cascade reactions, reductive Heck strategy

Tuesday, 14 March 2017

Asymmetric total synthesis of (-)-δ-lycorane

1H NMR
13C NMR



Org. Chem. Front., 2017, Advance Article
DOI: 10.1039/C7QO00021A, Research Article
Junliang Wang, Jianneng Li, Xianwang Shen, Cong Dong, Jun Lin, Kun Wei
A first asymmetric synthesis of (-)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction is reported.

Asymmetric total synthesis of (−)-δ-lycorane

Junliang Wang,ab   Jianneng Li,a   Xianwang Shen,a  Cong Dong,a   Jun Lin*ab and   Kun Wei*a  
*Corresponding authors
aSchool of Chemical Science and Technology, Yunnan University, P. R. China
bSchool of Chemical Science and Technology, Yunnan University, Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education), Kunming, P. R. China
E-mail: weikun@ynu.edu.cnlinjun@ynu.edu.cn
Fax: +86871 65031633
Tel: +86871 65031633
Org. Chem. Front., 2017, Advance Article
A first asymmetric synthesis of the lycorine-type Amaryllidaceae alkaloid (−)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction as a powerful tool to construct the skeleton of the alkaloid on the basis of unsaturated β-ketoester and nitroalkene is reported. The sequence afforded a highly functionalized intermediate with three stereogenic centres with high diastereoselectivity (>20 : 1 dr) and high enantioselectivity (92% ee) in one step, which was converted into (−)-δ-lycorane in eight steps.
The residue was purified by flash silica 8 Please do not adjust margins Please do not adjust margins Please do not adjust margins gel chromatography (DCM/MeOH = 10/1) to give (−)-δ-lycorane (9 mg, 72%) as a white solid.
m.p.: 125-126 °C; [α] = -51.9, (c = 0.1, CHCl3);
IR (thin film, ν cm -1): 3551, 3477, 3414 , 1637, 1617, 619, 473;
1H-NMR (500 MHz, CDCl3), δ (ppm): 6.79 (s, 1H), 6.68 (s, 1H), 5.93 (s, 2H), 4.29 (d, J = 14.5 Hz, 1H), 3.95 (dd, J = 11.0, 8.5 Hz, 1H), 3.68 (d, J = 14.5 Hz, 1H), 3.52 (dd, J = 11.5, 4.0 Hz, 1H), 3.25 (s, 1H), 2.50 (m, 1H), 2.41 (d, J = 2.0 Hz, 1H), 1.86 (m, 1H), 1.77 (m, 2H), 1.66 (d, J = 14.5 Hz, 1H), 1.59 (m, 2H), 1.37 (m, 2H);
13C-NMR (125 MHz, CDCl3) δ (ppm): 149.0, 146.5, 131.3, 120.5, 109.5, 106.9, 101.5, 66.3, 55.1, 50.7, 39.7, 34.5, 29.6, 29.0, 24.8, 20.4;
HRMS (ESI): m/z calcd for C16H20NO2 + [M + H]+ : 258.1489, found: 258.1488.
////(−)-δ-lycorane

4-Pentenoic acid, 5-(3,4-methylenedioxyphenyl)-3-oxo-, ethyl ester

str1
4-Pentenoic acid, 5-(3,4-methylenedioxyphenyl)-3-oxo-, ethyl ester
cas 860547-52-0
MF C14 H14 O5
4-Pentenoic acid, 5-(1,3-benzodioxol-5-yl)-3-oxo-, ethyl ester
Molecular Weight, 262.26
Melting Point (Experimental)
Value: 58-60 °C
Purification of the residue by flash column chromatography (10% ethyl acetate in hexanes) afforded the β-keto ester (12.0 g, 90%) as a pale yellow oil. Compound 3
1H-NMR (400 MHz, CDCl3), δ (ppm):12.00 (s, 0.4 H, enol OH), 7.52 (d, 1H, J = 16.0 Hz, C5 keto ), 7.35 (t, J = 15.6, 1H, C6’ keto), 7.05 (complex, 1.4H, C2’ keto, C2’ enol ), 7.03 (d, J = 12.8, 1H, C5’ keto), 6.97 (d, J = 8.0 Hz, 0.5H, C5’ enol), 6.83-6.78 (m, 1.5H, C6’, C5 and C2 enol), 6.65 (d, J = 16.0 Hz, 1H, C4 keto), 6.27 (d, J = 16 Hz, 0.5H, C4 enol), 6.02 (s, 2H, C7’ keto), 5.98 (s, 1H, C7’ enol), 4.22 (complex, 3H, COOCH2CH3, keto and enol), 3.66 (s, 2H, C2 keto), 1.29 (complex, 4.7H, COOCH2CH3 keto and enol);
13C-NMR (100 MHz, CDCl3), δ (ppm): 191.7, 172.8, 169.4, 167.5, 150.2, 148.8, 148.4, 148.2, 144.4, 136.4, 129.8, 128.4, 125.4, 123.5, 123.2, 119.9, 108.6, 108.5, 106.6, 106.1, 101.7, 101.4, 91.3, 77.3, 77.0, 76.7, 61.4, 60.1, 47.6, 14.2, 14.1.
 
1H NMR PREDICT
 
13C NMR PREDICT
 
/////////
Org. Chem. Front., 2017, Advance Article,
DOI: 10.1039/C7QO00021A
and

Sunday, 12 March 2017

1,3-Diphenylisoquinoline







1,3-Diphenylisoquinoline (3a). Pale-yellow solid (103.5 mg, 92%),

 mp 78-79 oC (lit.24,  73-74.5 oC). 24 J. D. Tovar and T. M. Swager, J. Org. Chem., 1999, 64, 6499

1H NMR (500 MHz, CDCl3) δ 8.25-8.23 (m, 2H), 8.15-8.14 (m, 1H), 8.09 (s, 1H), 7.95-7.93 (m, 1H), 7.84-7.83 (m, 2H), 7.70-7.67 (m, 1H), 7.59-7.50 (m, 6H), 7.44-7.40 (m, 1H);

13C NMR (125 MHz, CDCl3) δ 160.5, 150.3, 140.1, 139.8, 138.0, 130.4, 130.2, 128.8, 128.7, 128.6, 128.4, 127.7, 127.6, 127.2, 127.0, 126.0, 115.8.


Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids
Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00267J, Paper
Kun Hu, Linjun Qi, Shuling Yu, Tianxing Cheng, Xiaodong Wang, Zhaojun Li, Yuanzhi Xia, Jiuxi Chen, Huayue Wu
Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids for the synthesis of diverse isoquinolines in water.

Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

Kun Hu,a   Linjun Qi,a   Shuling Yu,a   Tianxing Cheng,a  Xiaodong Wang,a   Zhaojun Li,b   Yuanzhi Xia,a  Jiuxi Chen*a and   Huayue Wua  
 
*Corresponding authors
aCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China
E-mail: jiuxichen@wzu.edu.cn
bInstitute of Agricultural Resources and Regional Planning, Chinese Academy of Agricultural Sciences, Key Laboratory of Plant Nutrition and Fertilizer, Ministry of Agriculture, Beijing, China
Green Chem., 2017, Advance Article

DOI: 10.1039/C7GC00267J, 
A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)–cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.

Capture

STR1

1,3-Diphenylisoquinoline (3a). Pale-yellow solid (103.5 mg, 92%),
 mp 78-79 oC (lit.24,  73-74.5 oC). 24 J. D. Tovar and T. M. Swager, J. Org. Chem., 1999, 64, 6499
1H NMR (500 MHz, CDCl3) δ 8.25-8.23 (m, 2H), 8.15-8.14 (m, 1H), 8.09 (s, 1H), 7.95-7.93 (m, 1H), 7.84-7.83 (m, 2H), 7.70-7.67 (m, 1H), 7.59-7.50 (m, 6H), 7.44-7.40 (m, 1H); 
13C NMR (125 MHz, CDCl3) δ 160.5, 150.3, 140.1, 139.8, 138.0, 130.4, 130.2, 128.8, 128.7, 128.6, 128.4, 127.7, 127.6, 127.2, 127.0, 126.0, 115.8. 
//////// isoquinoline, pd-catalyzed, arylboronic acids