Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System
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A redox neutral rearrangement of an allene to a 1,3-diene by means of a unique palladium hydride complex is reported. The palladium hydride complex is generated from a simple Pd0 source and boric acid [B(OH)3], which is typically identified as a waste by-product of the Suzuki–Miyaura reaction. A mechanism for this transformation using this novel palladium hydride complex is presented; using a direct sample loop and flow injection ESI-HRMS analysis we have detected and identified key π-allylpalladium complexes that support the addition of the palladium hydride complex to the allene.
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2004 ◽
Vol 53
(4)
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pp. 381-387
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2018 ◽
Vol 84
(12)
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pp. 20-24
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1985 ◽
Vol 74
(8)
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pp. 886-888
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1991 ◽
Vol 45
(10)
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pp. 1581-1586
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