2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The Uses of 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used as a reagent to borylate arenes and to prepare fluorenylborolane.

It can also be used in the synthesis of following intermediates for generating conjugated copolymers:

• 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl1,3,2-dioxaborolane-2-yl)dibenzosilole.
• 3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.
• 2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.
• 2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole.

The Uses of 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The Iodo compound (308 mg, 0.513 mmol), the boronic ester (194 mg, 0.641 mmol), K3PO4 (327 mg, 1.539 mmol), XPhos (14.67 mg, 0.031 mmol), and Pd2(dba)3 (14.09 mg, 0.015 mmol) were combined in a microwave vial. The vial was purged with argon, after which time was added dioxane (3 mL) and H2O (0.5 mL) The reaction was irradiated in a microwave reactor at 120 C for 10 min. Additional boronic ester (50 mg) was added and the mixture was irradiated at 120 C for another 10 min. The mixture was then treated with aq 1N NaOH and extracted with EtOAc (50 mL). The org layer was dried (MgSO4), concentrated, and purified by flash chromatography (20% MeOH/DCM) to provide the product as a dark yellow solid. [177 mg, 53%]