Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene
The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this pro...
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Published in | Synlett Vol. 32; no. 5; pp. 511 - 516 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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Abstract | The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this process likely occurs through a rare protonolysis/second transmetalation event rather than by the well-established mechanism requiring the involvement of O-2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products could be obtained by employing dicyclohexyl(2 ',6 '-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand. |
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AbstractList | The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this process likely occurs through a rare protonolysis/second transmetalation event rather than by the well-established mechanism requiring the involvement of O-2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products could be obtained by employing dicyclohexyl(2 ',6 '-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand. |
Author | Sieber, Joshua D. Gargaro, Samantha L. Dunson, Bre'Shon |
Author_xml | – sequence: 1 givenname: Samantha L. surname: Gargaro fullname: Gargaro, Samantha L. organization: Virginia Commonwealth Univ, Dept Chem, 1001 West Main St, Richmond, VA 23284 USA – sequence: 2 givenname: Bre'Shon surname: Dunson fullname: Dunson, Bre'Shon organization: Virginia Commonwealth Univ, Dept Chem, 1001 West Main St, Richmond, VA 23284 USA – sequence: 3 givenname: Joshua D. surname: Sieber fullname: Sieber, Joshua D. email: jdsieber@vcu.edu organization: Virginia Commonwealth Univ, Dept Chem, 1001 West Main St, Richmond, VA 23284 USA |
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Cites_doi | 10.1002/anie.200900469 10.1021/om060380i 10.1021/ol034943n 10.1021/ja1108326 10.1016/j.jorganchem.2006.02.015 10.1039/b610213c 10.1016/j.jfluchem.2004.09.033 10.1021/Ja8074693 10.1002/adsc.200900587 10.1021/ja1073799 10.1021/cs300082f 10.1002/anie.201107017 10.1021/jacs.8b00400 10.1021/ja050583i 10.1021/ja903277d 10.1002/anie.200301753 10.1021/ja005622z 10.1021/ja505405u 10.1016/j.tet.2008.05.018 10.1002/cctc.201402326 10.1021/jacs.6b03283 10.1002/anie.201301737 10.1002/chem.200600616 10.1021/acscatal.8b02509 10.1055/s-0037-1611064 10.1002/chem.201001911 10.1021/acs.organomet.5b00567 10.1055/s-2004-831223 10.1021/jacs.7b07444 10.1002/ijch.201000074 10.1021/ja0569959 10.1126/science.1131943 10.1021/acscatal.7b02618 10.1016/j.tet.2007.12.036 10.1021/ja104297g 10.1021/ar800036s 10.1002/anie.200461189 10.1039/c2sc20903a 10.1016/j.tetasy.2013.06.007 10.1021/jacs.6b13384 10.1002/anie.200353615 10.1002/anie.201207750 10.1021/acs.joc.5b01005 10.1039/b711844a 10.1016/j.tet.2003.11.095 10.1126/science.aad6981 10.1002/chem.201201195 |
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Keywords | palladium catalysis DESIGN COMPLEXES CATALYST BASE MILD arylboronic acids cross-coupling CHEMISTRY COMPUTATIONAL CHARACTERIZATION bromobistrifluoromethylbenzene TRANSMETALATION PROCESS Suzuki-Miyaura reaction |
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Title | Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene |
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