A number of studies were conducted to demonstrate C-H activation for the construction of C-B bonds. Investigations revealed that the conversion of C-H bonds to C-B bonds was both thermodynamically and kinetically favorable. The reaction at a primary C-H bond of methane or a higher alkene B 2(OR)4 formed an alkylboronate ester R' -B(OR)2 and the accompanying borane H-B(OR2. The ester and the borane were formed on the basis of calculated bond energies for methylboronates and dioaborolanes. The rates of key steps along the reaction pathway for the conversion of a C-H bond in an alkane or arene to the C-B bond in an alkyl or arylboronate ester were favorable. These studies also highlighted the accessible barriers for C-H bond cleavage and B-C bond formation during the borylation of alkanes and arenes.

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C−H Activation for the Construction of C−B Bonds

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Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Suzuki–Miyaura (SM) cross-coupling is arguably the most widely-applied transition metal catalysed carbon–carbon bond forming reaction to date. Its success originates from a combination of exceptionally mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared and generally environmentally benign organoboron reagent. A variety of such reagents have been developed for the process, with properties that have been tailored for application under specific SM coupling conditions. This review analyses the seven main classes of boron reagent that have been developed. The general physical and chemical properties of each class of reagent are evaluated with special emphasis on the currently understood mechanisms of transmetalation. The methods to prepare each reagent are outlined, followed by example applications in SM coupling.

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Selection of boron reagents for Suzuki-Miyaura coupling

Transition metal chemistry of cyclopropenes and cyclopropanes.

A simple, general synthesis of 1-alkynyldiisopropoxyboranes

Organoboranes. 30. Convenient procedures for the synthesis of alkyl- and alkenylboronic acids and esters

Vinylic organoboranes. 13. A convenient stereospecific synthesis of (Z)-1-halo-1-alkenes from 1-alkynes via (E)-1-alkenylborane derivatives with halogens.

Vinylic organoboranes. 14. A stereospecific synthesis of (E)-1-halo-1-alkenes from 1-alkynes

Vinylic organoboranes. 7. Stereoselective synthesis of (E)-(1-substituted-1-alkenyl)boronic esters by the nucleophilic substitution of (Z)-(1-bromo-1-alkenyl)boronic esters with organolithium or Grignard reagents. Isolation and oxidation to ketones

N. G. Bhat

Papers

A simple, general synthesis of 1-alkynyldiisopropoxyboranes

Organoboranes. 30. Convenient procedures for the synthesis of alkyl- and alkenylboronic acids and esters

Vinylic organoboranes. 13. A convenient stereospecific synthesis of (Z)-1-halo-1-alkenes from 1-alkynes via (E)-1-alkenylborane derivatives with halogens.

Vinylic organoboranes. 14. A stereospecific synthesis of (E)-1-halo-1-alkenes from 1-alkynes

Vinylic organoboranes. 7. Stereoselective synthesis of (E)-(1-substituted-1-alkenyl)boronic esters by the nucleophilic substitution of (Z)-(1-bromo-1-alkenyl)boronic esters with organolithium or Grignard reagents. Isolation and oxidation to ketones