Ruthenium‐Catalyzed Reductive Arylation of N‐(2‐Pyridinyl)amides with Isopropanol and Arylboronate Esters
A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing group, is described. The N‐Py‐amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N‐Py‐1‐arylalkanamine reaction...
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Published in | Angewandte Chemie Vol. 131; no. 2; pp. 492 - 497 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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08.01.2019
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Abstract | A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing group, is described. The N‐Py‐amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N‐Py‐1‐arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN‐Py group with HCl. The 1‐aryl‐1‐chloroalkane products allow substitution and cross‐coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py‐NH2 by‐product can be recycled.
Eine reduktive Dreikomponenten‐Arylierung von Amiden mit stabilen Reaktanten (iPrOH und Arylboratester) in Gegenwart einer dirigierenden 2‐Pyridinyl(py)‐Gruppe (DG) wird beschrieben. Die N‐Py‐Amide lassen sich leicht aus Carbonsäuren herstellen, und die resultierenden N‐Py‐1‐Arylalkanamine können durch Substitution der HN‐Py‐Gruppe durch HCl leicht in die entsprechenden Chloride überführt werden. |
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AbstractList | Abstract
A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing group, is described. The N‐Py‐amide substrates are readily prepared from carboxylic acids and PyNH
2
, and the resulting N‐Py‐1‐arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN‐Py group with HCl. The 1‐aryl‐1‐chloroalkane products allow substitution and cross‐coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py‐NH
2
by‐product can be recycled. A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing group, is described. The N‐Py‐amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N‐Py‐1‐arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN‐Py group with HCl. The 1‐aryl‐1‐chloroalkane products allow substitution and cross‐coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py‐NH2 by‐product can be recycled. Eine reduktive Dreikomponenten‐Arylierung von Amiden mit stabilen Reaktanten (iPrOH und Arylboratester) in Gegenwart einer dirigierenden 2‐Pyridinyl(py)‐Gruppe (DG) wird beschrieben. Die N‐Py‐Amide lassen sich leicht aus Carbonsäuren herstellen, und die resultierenden N‐Py‐1‐Arylalkanamine können durch Substitution der HN‐Py‐Gruppe durch HCl leicht in die entsprechenden Chloride überführt werden. A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing group, is described. The N‐Py‐amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N‐Py‐1‐arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN‐Py group with HCl. The 1‐aryl‐1‐chloroalkane products allow substitution and cross‐coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py‐NH2 by‐product can be recycled. |
Author | Wybon, Clarence C. D. Meerpoel, Lieven Van Steijvoort, Ben F. Ronson, Thomas O. Prokopcová, Hana Wang, Xubin Renders, Evelien Maes, Bert U. W. |
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Cites_doi | 10.1002/ange.201709441 10.1002/anie.201612367 10.1002/chem.201402231 10.1002/chem.201702330 10.1021/ol034862r 10.1002/ange.201508575 10.1139/v01-150 10.1039/C7SC03613B 10.1021/jo502929x 10.1021/acs.orglett.5b00664 10.1002/anie.201508536 10.1039/C8CS00201K 10.1002/ange.201001127 10.1021/jacs.7b01705 10.1021/ja043334n 10.1002/ange.201612367 10.1021/cr400609m 10.1021/ja105194s 10.1021/ja012610k 10.1039/C7SC01175J 10.1002/adsc.201600378 10.1002/3527603832 10.1021/jo00220a040 10.1021/jo401521y 10.1002/ange.201508536 10.1021/om500603v 10.1002/chem.201404648 10.1002/anie.201001127 10.1021/acscatal.7b02599 10.1002/chem.201605657 10.1016/S0040-4039(01)90372-7 10.1021/acs.chemrev.6b00237 10.1039/C6CS00244G 10.1021/ja508067c 10.1021/ol3000316 10.1016/S1359-6446(05)03686-X 10.1021/ol4015317 10.1039/C6CC05318A 10.1039/C5GC01008J 10.1055/s-0035-1562442 10.1002/anie.201600097 10.1021/ja402922w 10.1002/ange.201301451 10.1016/j.tetlet.2017.09.030 10.1002/anie.201709441 10.1002/anie.201508575 10.1021/acs.chemrev.5b00203 10.1002/anie.201204098 10.1039/C5SC04671H 10.1021/acscatal.6b03277 10.1055/s-0036-1588080 10.1021/jo8007379 10.1039/C7QO00134G 10.1002/ange.201600097 10.1002/anie.201301451 10.1002/ange.201204098 10.1021/ja067612p 10.1039/c3ra43368d |
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Notes | These authors contributed equally to this work. |
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References | 2017; 7 2017; 8 2015; 17 2013; 3 2017; 4 2006; 11 2017; 23 2016; 52 2010 2010; 49 122 2004 2015; 80 2017 2017; 56 129 2012; 14 2016; 18 2008; 73 2014; 114 2014; 136 2013 2013; 52 125 2018; 47 2017; 139 2014; 20 1981; 22 2015 2015 2017; 54 127 23 2016; 7 2018; 8 2013; 15 2016 2016; 55 128 2015; 115 2017; 58 2013; 78 2012 2012; 51 124 2002; 124 2005; 127 2010; 132 2013; 135 2003; 5 2016 2016; 116 2016; 358 1985; 50 2001; 79 2016; 27 2016; 48 2006; 128 2014; 33 2016; 45 e_1_2_2_24_2 e_1_2_2_47_2 e_1_2_2_4_2 e_1_2_2_49_1 e_1_2_2_22_2 e_1_2_2_6_2 e_1_2_2_20_1 e_1_2_2_2_1 e_1_2_2_62_1 e_1_2_2_41_2 e_1_2_2_28_3 e_1_2_2_41_3 e_1_2_2_43_1 e_1_2_2_8_2 e_1_2_2_28_2 e_1_2_2_41_4 e_1_2_2_45_2 e_1_2_2_24_3 e_1_2_2_26_1 e_1_2_2_60_1 e_1_2_2_13_2 e_1_2_2_36_2 e_1_2_2_59_1 e_1_2_2_11_2 e_1_2_2_38_2 e_1_2_2_51_2 e_1_2_2_19_3 e_1_2_2_30_1 e_1_2_2_19_2 e_1_2_2_53_2 e_1_2_2_32_1 e_1_2_2_17_2 e_1_2_2_55_1 e_1_2_2_34_2 e_1_2_2_15_1 e_1_2_2_3_2 e_1_2_2_5_1 e_1_2_2_23_2 e_1_2_2_48_2 Murahashi S.-I. (e_1_2_2_57_1) 2004 e_1_2_2_21_2 e_1_2_2_1_1 e_1_2_2_40_2 e_1_2_2_42_1 e_1_2_2_29_2 e_1_2_2_7_2 e_1_2_2_7_3 e_1_2_2_44_2 e_1_2_2_9_3 e_1_2_2_27_1 e_1_2_2_9_2 e_1_2_2_25_2 e_1_2_2_46_2 e_1_2_2_61_1 e_1_2_2_12_3 e_1_2_2_37_1 e_1_2_2_12_2 e_1_2_2_39_2 e_1_2_2_10_1 e_1_2_2_52_1 e_1_2_2_50_2 e_1_2_2_31_1 e_1_2_2_18_2 e_1_2_2_56_1 e_1_2_2_16_2 e_1_2_2_33_2 e_1_2_2_54_2 e_1_2_2_33_3 e_1_2_2_58_1 e_1_2_2_14_2 e_1_2_2_35_2 |
References_xml | – volume: 115 start-page: 6621 year: 2015 publication-title: Chem. Rev. – volume: 17 start-page: 1696 year: 2015 publication-title: Org. Lett. – volume: 358 start-page: 2431 year: 2016 publication-title: Adv. Synth. Catal. – volume: 20 start-page: 17565 year: 2014 publication-title: Chem. Eur. J. – volume: 114 start-page: 5477 year: 2014 publication-title: Chem. Rev. – volume: 8 start-page: 7492 year: 2017 publication-title: Chem. Sci. – volume: 79 start-page: 1694 year: 2001 publication-title: Can. J. Chem. – volume: 52 125 start-page: 11726 11942 year: 2013 2013 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 45 start-page: 6685 year: 2016 publication-title: Chem. Soc. Rev. – start-page: 54 year: 2004 – volume: 135 start-page: 7442 year: 2013 publication-title: J. Am. Chem. Soc. – volume: 54 127 23 start-page: 13856 14062 12450 year: 2015 2015 2017 publication-title: Angew. Chem. Int. Ed. Angew. Chem. Chem. Eur. J. – volume: 18 start-page: 288 year: 2016 publication-title: Green Chem. – volume: 8 start-page: 203 year: 2018 publication-title: ACS Catal. – volume: 14 start-page: 950 year: 2012 publication-title: Org. Lett. – volume: 4 start-page: 1435 year: 2017 publication-title: Org. Chem. Front. – volume: 73 start-page: 5442 year: 2008 publication-title: J. Org. Chem. – volume: 56 129 start-page: 15901 16117 year: 2017 2017 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 80 start-page: 2861 year: 2015 publication-title: J. Org. Chem. – volume: 22 start-page: 1541 year: 1981 publication-title: Tetrahedron Lett. – volume: 5 start-page: 2687 year: 2003 publication-title: Org. Lett. – volume: 27 start-page: 2530 year: 2016 publication-title: Synlett – volume: 127 start-page: 5936 year: 2005 publication-title: J. Am. Chem. Soc. – volume: 48 start-page: 2829 year: 2016 publication-title: Synthesis – volume: 139 start-page: 5684 year: 2017 publication-title: J. Am. Chem. Soc. – volume: 128 start-page: 16516 year: 2006 publication-title: J. Am. Chem. Soc. – volume: 47 start-page: 6603 year: 2018 publication-title: Chem. Soc. Rev. – volume: 23 start-page: 9206 year: 2017 publication-title: Chem. Eur. J. – volume: 58 start-page: 4073 year: 2017 publication-title: Tetrahedron Lett. – volume: 33 start-page: 5643 year: 2014 publication-title: Organometallics – volume: 132 start-page: 12817 year: 2010 publication-title: J. Am. Chem. Soc. – volume: 3 start-page: 18787 year: 2013 publication-title: RSC Adv. – volume: 7 start-page: 1413 year: 2017 publication-title: ACS Catal. – volume: 51 124 start-page: 8314 8439 year: 2012 2012 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 52 start-page: 11967 year: 2016 publication-title: Chem. Commun. – volume: 124 start-page: 6043 year: 2002 publication-title: J. Am. Chem. Soc. – volume: 7 start-page: 3432 year: 2016 publication-title: Chem. Sci. – year: 2016 – volume: 78 start-page: 9803 year: 2013 publication-title: J. Org. Chem. – volume: 55 128 start-page: 4562 4638 year: 2016 2016 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 55 128 start-page: 387 395 year: 2016 2016 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 116 start-page: 12029 year: 2016 publication-title: Chem. Rev. – volume: 49 122 start-page: 6369 6513 year: 2010 2010 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 20 start-page: 8210 year: 2014 publication-title: Chem. Eur. J. – volume: 136 start-page: 14365 year: 2014 publication-title: J. Am. Chem. Soc. – volume: 11 start-page: 160 year: 2006 publication-title: Drug Discovery Today – volume: 15 start-page: 3452 year: 2013 publication-title: Org. Lett. – volume: 50 start-page: 3885 year: 1985 publication-title: J. Org. Chem. – volume: 8 start-page: 5536 year: 2017 publication-title: Chem. Sci. – volume: 56 129 start-page: 3655 3709 year: 2017 2017 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – ident: e_1_2_2_9_3 doi: 10.1002/ange.201709441 – ident: e_1_2_2_32_1 – ident: e_1_2_2_19_2 doi: 10.1002/anie.201612367 – ident: e_1_2_2_23_2 doi: 10.1002/chem.201402231 – ident: e_1_2_2_41_4 doi: 10.1002/chem.201702330 – ident: e_1_2_2_55_1 doi: 10.1021/ol034862r – ident: e_1_2_2_28_3 doi: 10.1002/ange.201508575 – ident: e_1_2_2_26_1 doi: 10.1139/v01-150 – ident: e_1_2_2_37_1 – ident: e_1_2_2_14_2 doi: 10.1039/C7SC03613B – ident: e_1_2_2_13_2 doi: 10.1021/jo502929x – ident: e_1_2_2_22_2 doi: 10.1021/acs.orglett.5b00664 – ident: e_1_2_2_15_1 – ident: e_1_2_2_41_2 doi: 10.1002/anie.201508536 – ident: e_1_2_2_36_2 doi: 10.1039/C8CS00201K – ident: e_1_2_2_24_3 doi: 10.1002/ange.201001127 – ident: e_1_2_2_48_2 doi: 10.1021/jacs.7b01705 – ident: e_1_2_2_62_1 doi: 10.1021/ja043334n – ident: e_1_2_2_19_3 doi: 10.1002/ange.201612367 – ident: e_1_2_2_3_2 doi: 10.1021/cr400609m – ident: e_1_2_2_42_1 doi: 10.1021/ja105194s – ident: e_1_2_2_54_2 doi: 10.1021/ja012610k – ident: e_1_2_2_29_2 doi: 10.1039/C7SC01175J – ident: e_1_2_2_46_2 doi: 10.1002/adsc.201600378 – ident: e_1_2_2_52_1 – start-page: 54 volume-title: Ruthenium in Organic Synthesis year: 2004 ident: e_1_2_2_57_1 doi: 10.1002/3527603832 contributor: fullname: Murahashi S.-I. – ident: e_1_2_2_11_2 doi: 10.1021/jo00220a040 – ident: e_1_2_2_59_1 doi: 10.1021/jo401521y – ident: e_1_2_2_41_3 doi: 10.1002/ange.201508536 – ident: e_1_2_2_21_2 doi: 10.1021/om500603v – ident: e_1_2_2_17_2 doi: 10.1002/chem.201404648 – ident: e_1_2_2_24_2 doi: 10.1002/anie.201001127 – ident: e_1_2_2_49_1 – ident: e_1_2_2_43_1 – ident: e_1_2_2_38_2 doi: 10.1021/acscatal.7b02599 – ident: e_1_2_2_35_2 doi: 10.1002/chem.201605657 – ident: e_1_2_2_27_1 – ident: e_1_2_2_60_1 doi: 10.1016/S0040-4039(01)90372-7 – ident: e_1_2_2_1_1 doi: 10.1021/acs.chemrev.6b00237 – ident: e_1_2_2_4_2 doi: 10.1039/C6CS00244G – ident: e_1_2_2_45_2 doi: 10.1021/ja508067c – ident: e_1_2_2_16_2 doi: 10.1021/ol3000316 – ident: e_1_2_2_58_1 doi: 10.1016/S1359-6446(05)03686-X – ident: e_1_2_2_25_2 doi: 10.1021/ol4015317 – ident: e_1_2_2_18_2 doi: 10.1039/C6CC05318A – ident: e_1_2_2_20_1 – ident: e_1_2_2_31_1 doi: 10.1039/C5GC01008J – ident: e_1_2_2_47_2 doi: 10.1055/s-0035-1562442 – ident: e_1_2_2_7_2 doi: 10.1002/anie.201600097 – ident: e_1_2_2_44_2 doi: 10.1021/ja402922w – ident: e_1_2_2_33_3 doi: 10.1002/ange.201301451 – ident: e_1_2_2_8_2 doi: 10.1016/j.tetlet.2017.09.030 – ident: e_1_2_2_9_2 doi: 10.1002/anie.201709441 – ident: e_1_2_2_28_2 doi: 10.1002/anie.201508575 – ident: e_1_2_2_30_1 doi: 10.1021/acs.chemrev.5b00203 – ident: e_1_2_2_12_2 doi: 10.1002/anie.201204098 – ident: e_1_2_2_56_1 – ident: e_1_2_2_6_2 doi: 10.1039/C5SC04671H – ident: e_1_2_2_40_2 doi: 10.1021/acscatal.6b03277 – ident: e_1_2_2_39_2 doi: 10.1055/s-0036-1588080 – ident: e_1_2_2_51_2 doi: 10.1021/jo8007379 – ident: e_1_2_2_34_2 doi: 10.1039/C7QO00134G – ident: e_1_2_2_5_1 – ident: e_1_2_2_2_1 – ident: e_1_2_2_7_3 doi: 10.1002/ange.201600097 – ident: e_1_2_2_33_2 doi: 10.1002/anie.201301451 – ident: e_1_2_2_12_3 doi: 10.1002/ange.201204098 – ident: e_1_2_2_61_1 doi: 10.1021/ja067612p – ident: e_1_2_2_10_1 – ident: e_1_2_2_50_2 – ident: e_1_2_2_53_2 doi: 10.1039/c3ra43368d |
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Snippet | A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing group, is... Abstract A new three‐component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2‐pyridinyl (Py) directing... |
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SubjectTerms | Amide Amides Amine Aromatic compounds Arylierung Carboxylic acids Chemical reactions Chemistry Esters Mehrkomponenten-Reaktionen Organochlorine compounds Reaction products Ruthenium Substitution reactions Substrates |
Title | Ruthenium‐Catalyzed Reductive Arylation of N‐(2‐Pyridinyl)amides with Isopropanol and Arylboronate Esters |
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