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Mechanistic Insight into the Nickel‐Catalyzed Cross‐Coupling of Aryl Phosphates with Arylboronic Acids: Potassium Phosphate is Not a Spectator Base but is Involved in the Transmetalation Step in the Suzuki–Miyaura Reaction
Author(s) -
Liu Liu Leo,
Zhang Shuangyan,
Chen Hu,
Lv Ye,
Zhu Jun,
Zhao Yufen
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300688
Subject(s) - transmetalation , aryl , base (topology) , chemistry , catalysis , boron , combinatorial chemistry , potassium , computer science , organic chemistry , mathematical analysis , alkyl , mathematics
Spectator or actor? Density functional theory calculations were performed to examine the role of the base in the nickel‐catalyzed cross‐coupling of aryl phosphates with arylboronic acids. Potassium phosphate was found to not act as a spectator base but was involved in the transmetalation step, as shown by a lower barrier than that of a base‐free process, owing to the activation of the carbonboron bond by the base. Further experimental observations support the theoretical findings.