TY - JOUR AU - Al-Jawaheri, Yassir; Turner, Matthew; Kimber, Marc C. TI - Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System SN - 0039-7881 SN - 1437-210X PY - 2018 JO - Synthesis JF - Synthesis LA - EN VL - 50 IS - 12 SP - 2329 EP - 2336 ET - 2018/05/17 DA - 2018/05/30 KW - allene KW - 1,3-diene KW - palladium KW - boric acid KW - palladium hydride complex AB - 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. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1591580 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0036-1591580 ER -