A new approach to carbon–carbon bond formation: development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes
Alkenes are attractive starting materials for organic synthesis and the development of new selective functionalization reactions is desired. Previously, our laboratory discovered a unique Pd-catalyzed hydroalkoxylation reaction of styrenes containing a phenol. Based upon deuterium labeling experimen...
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| Veröffentlicht in: | Tetrahedron 2009-06, Vol.65 (26), p.5074-5083 |
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| creator | Gligorich, Keith M. Iwai, Yasumasa Cummings, Sarah A. Sigman, Matthew S. |
| description | Alkenes are attractive starting materials for organic synthesis and the development of new selective functionalization reactions is desired. Previously, our laboratory discovered a unique Pd-catalyzed hydroalkoxylation reaction of styrenes containing a phenol. Based upon deuterium labeling experiments, a mechanism involving an aerobic alcohol oxidation coupled to alkene functionalization was proposed. These results inspired the development of a new Pd-catalyzed reductive coupling reaction of alkenes and organometallic reagents that generates a new carbon–carbon bond. Optimization of the conditions for the coupling of both organostannanes and organoboronic esters is described and the initial scope of the transformation is presented. Additionally, several mechanistic experiments are outlined and support the rationale for the development of the reaction based upon coupling alcohol oxidation to alkene functionalization.
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| doi_str_mv | 10.1016/j.tet.2009.03.096 |
| format | Article |
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| ispartof | Tetrahedron, 2009-06, Vol.65 (26), p.5074-5083 |
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| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Catalysis Chemistry Cross-coupling Exact sciences and technology Kinetics and mechanisms Mechanism Molecular Oxygen Noncondensed benzenic compounds Organic chemistry Palladium Preparations and properties Reactivity and mechanisms |
| title | A new approach to carbon–carbon bond formation: development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes |
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