Fig. 1: Multifaceted reactivity of organometallic reagents. | Nature Communications

Fig. 1: Multifaceted reactivity of organometallic reagents.

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

Fig. 1

a Representative elementary reactions of polarized organometallic reagents (e.g., organolithium, organomagnesium reagents, etc.) and exemplified strategies for delivering sensitive organometallic reagents. b Organoboronates are typically used as a cross-coupling partner for C−C bond constructions with boron unit [B] as a leaving group. c In the presence of alkali-metal alkoxides, benzylic (or allylic) boronates might be considered as both superbase precursors and boron sources through the in situ heterolysis of the C−B bond. d Outline of the possible transformations using organoboronates/alkali-metal alkoxides combinations as reactive organometallic reagents via deprotonative metalation, metal-halogen exchange or anionic polymerization, in analogy to sensitive organolithiums, organomagnesiums, etc.

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