Fig. 2: Exploration of the superbase reactivity of organboronates, application for aromatic C−H borylation reaction, and mechanistic insight. | Nature Communications

Fig. 2: Exploration of the superbase reactivity of organboronates, application for aromatic C−H borylation reaction, and mechanistic insight.

From: Organometallic-type reactivity of stable organoboronates for selective (hetero)arene C−H/C-halogen borylation and beyond

Fig. 2

a Computational screening for the possible organoboronates/KOtBu combination, which could undergo C−B bond heterolysis to generate carbanion species (∆Gǂ: activation barrier; ∆G: reaction energy). b Experimental evaluation of the reactivity of different organoboronates for the C−H borylation of N-methylindole 2. c 1H and 11B NMR (400 MHz, THF-d8) studies on the model reaction. Numbers within the parentheses are the boron resonances. d Computed pathways [M06-2X/def2-TZVPP, SMD(THF)//M06-2X/def2-SVP, SMD(THF)] for C−H borylation of N-methylindole with benzylic boronate 1c/KOtBu combination. The Gibbs free reaction energies (relative to 1c) and barriers (labeled with an asterisk, relative to Int1) are in kcal mol-1. KIE: Kinetic Isotope Effect (KIEexp.: experimental measured KIE; KIEcal.: computed KIE with TS2-3). Color code: H, white; C, gray; B, pink; O, red; N, blue; K, purple.

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