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. Author manuscript; available in PMC: 2015 Feb 28.
Published in final edited form as: Nature. 2014 May 15;509(7500):299–309. doi: 10.1038/nature13274

Figure 3. Milestones in cross-coupling reactions of aryl ethers and esters.

Figure 3

a, Negishi-type, nickel-catalyzed biaryl formation from aryl ethers (8) and organomagnesium (Grignard) reagents (9). b, Suzuki–Miyaura-type, nickel-catalyzed biaryl synthesis from aryl ethers (8) and boronic esters (10). c, Suzuki–Miyaura-type, nickel-catalyzed biaryl synthesis utilizing aryl esters (11) and aryl boronic acids (12) or aryl boroxines (13). Ph, phenyl; t-Bu, tert-butyl; Et, ethyl; cod, 1,5-cyclooctadiene; i-Pr, isopropyl; Mes, 2,4,6-trimethylphenyl.