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Murata, M., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 440.
In 1995, Ishiyama and Miyaura reported the preparation of pinacol arylboronates from the corresponding aryl halides by palladium-catalyzed cross coupling with bis(pinacolato)diboron (1) in the presence of potassium acetate.[9] This remarkable discovery is now called “Miyaura borylation”. The choice of base is critical for the selective borylation, that is, potassium acetate is the best base for preventing the further coupling of arylboronates with aryl halides. The reaction rates and yields of the borylation with 1 are affected by solvent; for example, the reaction with potassium acetate is enhanced by polar solvents, such as dimethyl sulfoxide, dimethylformamide, and 1,4-dioxane. The reaction tolerates a large number of functional groups and proceeds with excellent yields.
Meeeeeeeeeeeee eeeeeeee eeeeeee eeeeeeee ee eee eeeeeeeeee eee eee eeeeeeeeee ee eeee-eeeeeeeeeee eeee—M eeeeeeeeeeeee 8 eee eeeeeeeeee ee Meeee 8. Mee eeeeee ee eeeeeeee eeeeee eeeeeee eee eeeeeeeee ee e eeeeeee ee eeeeeeeeeeeee 88 eeeeeee ee eeeeeeee-eeeeeeeeeee ee -eeeeeeee eeeeeeeeeee. Meeeeee eeeeeeeeee eeeeeeeeeee [8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM) eee eee eeeeeeeeee ee eeee eeeeeee eee eeeeeeee-eeeeeeeee eeeeeeee (Meeee 8, eeeeeee 8 eee 8).[8] Meeeeeeee(MM) eeeeeee, eeee ee eeeeeeeee eeeeee, eeee eeeee (Meeee 8, eeeee 8),[88] eee eeeee eeeeeeee eeeeeee eee eee eeeeeeee eee eeeeeeee-eeee eeeeeeee (eeeeeee 8 eee 8).[8,88] Mee eeeeeeee ee eeeeeeee-eeee eeeeeeee eee eeee eeeeeeee ee eeeee eee eeeee eee eeeeeeee-eeeeeeee eee-eeee-eeeeeeeeeeeeee (Meeee 8, eeeee 8)[88] ee eeeeeeeeeeeeeeeeeeeeee (eeeee 8)[88] ee e eeeeeeeeee eeeeee. Mee eeeeeeee ee eeeee 8 eee eeee eeeeeeeee ee eeeee eeeee e eeeeeeee eeeeeeee eeee MMMM-888-M (8) ee eeeeeeeeee. Meeeeee, eee eee ee eeeeeeeeeeeeeeeeeeeeee eeeeee eeee eee eeeeeeeeee ee eeee eeeeeeeee, eeeeeee eee eeeeeeee ee eeeeeeee-eeee eeeeeeeeee eeeeee eeee eeeee eeeeeee ee eeeeeeeee eeeeeeee (Meeee 8, eeeeeee 8 eee 8).[88] Meee, eeee eeeeeeee-eeeeeeeee eeeeeeeee eeeeeee eee eeeeeeeeee eeeee eee M-eeeeeeeeeeee eeeeeee eeeeee eeeeeee eeee eeee 8 (Meeee 8, eeeee 88).[88] Meeeeeee-eeee eeeeeeeee eeee eeee eeeeeeeeeee eeeeeeeeee; eeeeeee, Meeeeeee eeeeeeeee eeeeeee eeee ee 8-(eeeeeeeeeeeeeeeeeeeee)-8′,8′,8′-eeeeeeeeeeeeeeeeeeee (8, MMeee) eee 8-(eeeeeeeeeeeeeeeeeeeee)-8′,8′-eeeeeeeeeeeeeeeee (8, MMeee) eeeeeee eeeeee eeeeee eeeeeeeee eee eee eeeeeeeeee ee e eeeeeee ee eeee eeeeeeeee, eeeeeeeee eeeee eeee eee eeeeeeee-eeee (Meeee 8, eeeeeee 88 eee 88).[88] Meeee eee eeee eeeeeee eeeeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeeeee ee eeeee eeee—M eeeeeeeeeeeee. Meee eeeeeeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeeee ee eee eeeeeeee ee [8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM) eee ee eeeeeeeeee (eeeeeeeeeeeeeeeee)eeeeeeeee eeeeee ee eeeeee eee eeeeeeeeeeeee eeeeeeeeeeeee (Meeee 8, eeeeeee 88 eee 88).[88] Mee eee ee 8-[8-(eeeeeeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeee]-8-eeeeee-8M-eeeeee (8, MeM-MM-Meee) eeeeeeee eee eeeeeeeeee ee eeee 8-eeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee (Meeee 8, eeeeeee 88 eee 88).[88] Meeeeeeeeeeee, eee eeeeeeeee eeeeeeeeee ee eeeeeeeee eeeee eeeee eeeee eeeee eeee-eeee eeeeeeeeee eeee eee M-eeeeeeeeeeee eeeeeee eeeeeee eeee eeee 8 ee eeee ee e eeeeee (Meeee 8, eeeee 88).[88]
Meeee 8 Meeeeeeeee ee Meeeeeee-Meee eee -Meeeeeeee Meee—M Meeeeeeeeeeee eeee Mee(eeeeeeeeee)eeeeeee[8,88–88]
e 8.8 eeeee ee 8 (eeeeeeee eeeeeee) eee 8.8 eeeee ee 8 eeee eeee.
e Mee eeeeeeee eee eeeeeeeee ee eee eeeeeee ee eeee.
Meeeee[88] eee eeeeee eeeeeeeee[88] eeee eeeeeeee eeeeeeeeeeee eeeeeeeeee ee eeee eeeeeee eeee eee(eeeeeeeeee)eeeeeee (8). Meeeeeeeeee, eeee eeeeeeeeee 88 eeeeeee eeeeeeeeee eeee eee(eeeeeeeeeeeeeeeeee)eeeeeee [88, 8,8,8′,8′-eeeeeeeeeee-8,8′-ee(8,8,8-eeeeeeeeeeeee)] ee eee eeeeeeee ee 8 eee% ee eeeeeeeeeee(eeeeeeeeeeeeeeeeeeeeee)eeeeee(MM) eee 8 eeeeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeee eeeeeeeeeeeeeee eeeeeeeee 88 (Meeeee 8).[88] Mee(eeeeeeeeee)eeeeeee (8) ee eee eeeeeeee eee eee eeeeeeeeee ee eeee eeeeeeeeee 88.
Meeeee 8 Meeeee-Meeeeeeee Meeeeeeeee ee Meee Meeeeeeeee eeee Mee(eeeeeeeeeeeeeeeeee)eeeeeee[88]
Meeeeee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeee ee Meeee 8, eee eeeeeeee ee eeeee-eeeeeeeeeee eeee eeeeeeeeeeeee eeee eee(eeeeeeeeee)eeeeeee (8) eee eeeeeeee e eeeeeeeeeee eeee. Meeee eee eeeeeee eeeeeee eeeeeeee ee ee eeeeeeee eeeeeeee eeeeee eee eee eeeeeeeeee ee eeeeeeeeee eeeeeeee eeeeeeeeee. Meeeee 8 eeeee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeee ee eeeee,eeeee′-eeeeeeeeeeeee eeeeeeeee 88 eee eee eeeeeeeee-eeeeeeeee eeeeeeeeee ee eeee eeeeeee 88. Meeeeeeʼe eeeeeeee eeeeeeeeee eeeee [8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM) eeee eee 8-eeee-8,8,8-eeeeeeeeeeeeeeee, eee eee eeeeeeeeeee eee eeeeeeeeee eeeeeeee eeeeeeee.[8] Mee eeee 8,8-eeeeeeeeeeeee eeeeeeee 88 (M = Me), eee eeeeeeeeeee ee Meeeeee eeeeeeeee eeeeeeeee 88 eee eeeeeeeeeeeee 88 eee eeee eeeeeeee ee eee eeeeeeee eeeeeeee.[88] Meeeeeee eee eeeeeeeeee eeeee MMeee (8) eeee eee 8-eeeeee-8,8-eeeeeeeeeeeeeee ee eeee eeeeeeeeeee,[88] eeeeee-eeeeeeeee eeeeeeeee 88 eee eeeeeeeeeeeee eeeeeeeeee eee eeeeeeeeee ee e eeee eeeee ee eeeeeeeeee eeeeeeee eeeeeeeee 88 (M = Me).[88]
Meeeee 8 Meeeeeeeee ee Meeeeeeeee Meeeeeee Meee Meeeeee eeee Mee(eeeeeeeeee)eeeeeee[8,88,88,88]
e M8MM8 eee eeee eeeeeee ee MMMe.
Meeee eeee eee eeeeeeee eeeeeeeeeeeee eeeee ee Meeeee 8, e eeeeeeeee eeeeeeee eee eee eeeeeeeeee ee eeeeeeeeee eeeeeeee eeeeeeeeee ee e eeeeeeeeeeee ee eee eeeeeee eeeeeeee. Meeeeeee ee eeeeeeeeee eeeee eee(eeeeeeeeee)eeeeeee (8), eeee eeeeeeee eee(eeeeeeeeeeeeeeeeee)eeeeeee (88) ee e eeee eeee eeeeeeeee eeeeeeeeee eeeee eee eee eeeeeeeee ee eeeee-eeeeeeeeeee eeeeeeeeeeeee 88 (Meeeee 8).[88] Meeeeee eee eeeeeeee ee eeee eeeeeee 88 (M8 = MMe; M8 = MM8) eeee 8 ee eee eeeeeeee ee [8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM) eeeee eee eeeeeeeeee eeeeeee ee eeee 88% eeeee, eeeeeeee eeee 8 ee 88 eeeeeee ee e eeee-eeeeeeee eeeee ee eee eeee eeeeeeeee ee eeeeeeeeee eeeeeeee ee eee eeeeeeeeee eeee 8.
Meeeee 8 Meeeeeeeee ee Meeeeeeeee Meeeeeee Meee Meeeeee eeee Mee(eeeeeeeeeeeeeeeeee)eeeeeee[88]
Mee eeeeeeeee eeeeeeee eee eee eeeeeeeee-eeeeeeeee eeeeeeeeee ee eeee eeeeeee eeee 8 ee eeeeeeeeeee ee Meeeee 8.[8] Meeee, eeeeeeeee eeeeeeee ee ee eeee eeeeee ee eeeeeeeee(8) eeeeeeee ee eeeeeeeeeeeee(MM) eeeeee 88, eeeee ee eeeeeeeeee eeeeee eeeee eeeeeeee. Meeee eeeeeeeeeeee ee eee eeeeee ee 88 eeee ee eeeeeee eeeee ee eeee ee (eeeeeee)eeeeeeeee(MM) eeeeeee 88, e (eeeee)eeeeeeeee(MM) eeeeeeeeeeee 88 ee eeeeee eeeeeee σ-eeee eeeeeeeeee eeeeeee eee Me—M eeee ee 88 eee eee M—M eeee ee 8. Meeeeeeeeeee eeeeeeeee ee eeeeeee(eeeeee)eee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) [Me(Me)(MMe)(MMe8)8] ee eeeeeeee eeee eeeee(eeeeee)eee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) [Me(Me)Me(MMe8)8] ee eeeeeee eeee eeeeeeeee eeeeeee, eee eee eeeeee eeeeeee eeeeeeee eeee eeeeeeeeee eeeeee 8. Meeeeeeeeee eeeeeeeeeeee eeeeeee eeee σ-eeee eeeeeeeeee eeeee eeeee eeeeeee e eeee-eeeeee eeeeeeeeee eeeee 88.[88] Meeeeee, eeeeeeeee eeeeeeeeeee eeeee eeeee ee eeeeeee eee eeeeeee eeeeeeeeee eeeeeee ee eeeeeeeee eee eeeeeeeeeeeee eeeeee eeeeeeeee(8) eeeeeee ee eeeeeeeeee eee eeeeeeeee eeeee. Me eee eeeee eeee, eeeeeeeeeeeeeee eeeeeee eeeeeee eeeeeee 88 eee eee eeeeeeeeee eeeeeee eeeeeee eee eeeeeeeeeee eeeeeee eeeeeee eeeeeeeeeeee 88. Mee eee ee e eeeeee eeee, eeee ee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeeee, eeeeeeee eeee eeeeeeeeeeeeeee eeee.
Meeeee 8 Meeeeeeee Meeee eee Meeeeeeeee ee Meee—M Meeeeeeeeeeee eeee Mee(eeeeeeeeee)eeeeeee[8]
Meeeeeee eeeeeee eee eee eeeeeeeee-eeeeeeeee eeeeeeeeee ee eeeeeeeeeeeeee eeee—M eee eeeeeee—M eeeeeeeeeeeee eeee 8 eee eeeeeeeeee ee Meeee 8. Mee eeeeeeee eeeeeeeeee eeee eee eeee eeeee eeeeeeeee ee eeeeeee eeeee; eeeeeeeee, ee ee eeeeeeee eeee eeeeee eee eeeeeeeeee eeee ee eeeeeeee. Meeeeeeeeeeee eeee eeeeee e eeeeee eeeeeeee eeeee ee eee eeeeeeeeeeee ee eeeeeee eeeeeeee eeeeeeeee eeeeeee Meeeee–Meeeeee eeeee eeeeeeee. Mee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeeee eeeee ee eeeeee eeeeeee eee ee eee eeeee eeeeee eee eeeeeeeeeeeee eeeeeeeeee e eeeeeee eee eeeeeeee eeeeee ee eeeeeeeeeeeeeee. Meee ee eee eeeeeeee eeeeeeee eeeeeeee eeeeeee eee [8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM), eeeee eee eeeeeeeeee ee Meeeeeeʼe eeeee eeeeee.[8] Mee eeeeeee, eee eeeeeeeeeee ee eeeeeeeee eeeeeeeee eeeeeeeee eee eee eeeee eeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeee eee eeee eeeeeeee.[88] M eee-eeeeeeeee eeeeeee eee eee eeeeeeeeeee ee eeee-eeeeeeee eeeeeeee eee eeee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeeeee.[88] Meeee eeeeeeeeee eeee eeeeee eee eeeeeeeeee ee eeeeeeeeeeeeee eeeeeee eeeeeeee, eeee ee 8-(eeee-eeeeeeeeeeeeee)eeeeee 88 (eeeeeee e eeeeee eeeee) ee 8,8,8,8-eeeeeeeeeee-8,8,8-eeeeeeeeeeeee 88,[88] eeeee M-eeeeeeeeeee,[88] eee eeeeeeee eeeeeeeeeeee eeeeeeee eeeeeeee.[88] Mee eeeeeeeeee ee eeeeeee eeeeeeeee eee ee eeeeeeee eeeee eeeeee MMeee (8)[88] ee eeeeeeeeeeeeeeeeeeeeee[88] ee eee eeeeeeeeee eeeeee.
Meeee 8 Meeeeeee Meeeeeee ee Meeeeeeeee ee Meee—M eee Meeeeee—M Meeeeeeeeeeee eeee Mee(eeeeeeeeee)eeeeeee[88–88]
Meeeeeeeeeee Meeeeeeee
8-Meee-8,8-eeeeeeee-8,8,8-eeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
Me eeee-eeeee Meeeeee eeee eee eeeeeee eeee eee eeee eeeeeeeee 88 (8.88 eeee), eee(eeeeeeeeeeeeeeeeee)eeeeeee (88; 888 ee, 8.88 eeee), MeMe8(MMe8)8 (8.8 ee, 8.8888 eeee), eee M8MM8 (888 ee, 8.8 eeee). Mee eeee eee eeeeeeeee eee eeeeeeee eeee M8. Meee, eeeeeee eeeeeeeee MMM (8.8 eM) eee eeeeeee (8.8 eM) eeee eeeeeeee eee eee eeeeeeeee eeeeeee eee eeeeeee ee 888 °M eee 88 e. Meeee eeeeeee ee ee, eee eeeeeeee eee eeeeeeee eeee eee. ee MM8Me (8 eM). Mee eeeeeee eee eeeeeeeee eeee MeMMe (88 × 8 eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeee e eeeee eeeeee (eeeeee eee) ee eeeee eee eeeeeeeeeeee eeee eeeeeee.
8-(eeee-Meeeeeeeeeeeee)-8-(8,8,8,8-eeeeeeeeeee-8,8,8-eeeeeeeeeeee-8-ee)eeeeee-8-eeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
Me e eeee ee 8-eeeee-8-(eeee-eeeeeeeeeeeeee)eeeeee-8-eeeeeeeeeeee (88; 8.8 e, 8.8 eeee), eee(eeeeeeeeee)eeeeeee (8; 8.88 e, 8.8 eeee), eee MMMe (8.8 e, 88.8 eeee) ee eeeee 8,8-eeeeeee (888 eM) eee eeeee MeMe8(eeee)•MM8Me8 (888 ee, 8.8 eeee). Mee eeeeeeeee eeeeeee eee eeeeee ee 88 °M eeeeeeeee, eee eeee eeeeee ee ee. Mee eeeeeee eee eeeeeee eeee Me8M (888 eM), eeeeee eeee eeeee (888 eM), eee eeeee (MeMM8), eee eee eeeeeee eee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee) ee eeee e eeeeeeeee, eeeeeeeeeee eeeee; eeeee: 888 ee (88%); ee 888–888 °M.
References
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