Borylation using group IV metallocene under mild conditions
•We developed a borylation reaction of diazonium salts.•Di(isopropyl)aminoborane is used as borylation agent.•Mechanism is thought to proceed through a radical pathway.•Zr- and Ti-centered metallocenes were the most efficient initiators.•Many boronates were obtained including with halide substitutio...
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| Published in | Tetrahedron letters Vol. 55; no. 10; pp. 1702 - 1705 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
05.03.2014
Elsevier |
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| Online Access | Get full text |
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| Abstract | •We developed a borylation reaction of diazonium salts.•Di(isopropyl)aminoborane is used as borylation agent.•Mechanism is thought to proceed through a radical pathway.•Zr- and Ti-centered metallocenes were the most efficient initiators.•Many boronates were obtained including with halide substitution.
A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway. |
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| AbstractList | A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway. •We developed a borylation reaction of diazonium salts.•Di(isopropyl)aminoborane is used as borylation agent.•Mechanism is thought to proceed through a radical pathway.•Zr- and Ti-centered metallocenes were the most efficient initiators.•Many boronates were obtained including with halide substitution. A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway. A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway. (C) 2014 Elsevier Ltd. All rights reserved. |
| Author | Vaultier, Michel Pucheault, Mathieu Marciasini, Ludovic D. |
| Author_xml | – sequence: 1 givenname: Ludovic D. surname: Marciasini fullname: Marciasini, Ludovic D. – sequence: 2 givenname: Michel surname: Vaultier fullname: Vaultier, Michel – sequence: 3 givenname: Mathieu surname: Pucheault fullname: Pucheault, Mathieu email: m.pucheault@ism.u-bordeaux1.fr |
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| CitedBy_id | crossref_primary_10_1002_anie_201612535 crossref_primary_10_1002_ejoc_202201399 crossref_primary_10_1021_acscatal_8b02009 crossref_primary_10_1246_cl_200213 crossref_primary_10_1002_chem_201304861 crossref_primary_10_1021_acs_accounts_7b00566 crossref_primary_10_3184_174751918X15362432558247 crossref_primary_10_1002_ange_201612535 crossref_primary_10_1021_acs_orglett_5b01620 crossref_primary_10_1021_acsomega_2c01461 crossref_primary_10_1021_acs_chemrev_0c01030 crossref_primary_10_1002_chin_201432197 crossref_primary_10_1002_adsc_201701030 crossref_primary_10_1021_acs_chemrev_9b00384 crossref_primary_10_1002_ejoc_201900013 crossref_primary_10_1021_acs_orglett_4c01448 crossref_primary_10_1016_j_tet_2018_11_036 crossref_primary_10_1021_acs_orglett_0c00908 crossref_primary_10_1039_C9SC03765A crossref_primary_10_1002_adsc_201401153 crossref_primary_10_1016_j_tet_2014_04_036 crossref_primary_10_1016_j_tetlet_2016_02_097 crossref_primary_10_1021_acs_joc_2c00697 crossref_primary_10_1007_s11030_021_10295_3 |
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| Keywords | Titanium Boron Zirconium Metallocene Radical HALIDES CROSS-COUPLING REACTION MECHANISM COMPLEXES NANOCRYSTALS SALTS FUNCTIONALIZATION PALLADIUM-CATALYZED BORYLATION TRANSITION-METAL CHEMISTRY |
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| Snippet | •We developed a borylation reaction of diazonium salts.•Di(isopropyl)aminoborane is used as borylation agent.•Mechanism is thought to proceed through a radical... A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs... |
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| SubjectTerms | Boron Catalysis Chemistry Chemistry, Organic Derivatives Metallocene Metallocenes Pathways Physical Sciences Radical Radicals Reaction mechanisms Science & Technology Tetrahedrons Titanium Transesterification Zirconium |
| Title | Borylation using group IV metallocene under mild conditions |
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