The Chemistry of Organoboron Species: Classification and Basic Properties

Abstract

Organoboron chemistry began more than 150 years ago when the synthesis and reactivity of triethylborane was described. Organoboron chemistry research has rapidly increased within the past few decades due to the increased usage of organoboron compounds in organic synthesis and biomedical applications. This chapter gives an overview of the general physical and chemical characteristics of select organoboron compounds. Only compounds incorporating a boron–carbon bond are discussed in detail.

Organoboronic acids/esters as effective drug and prodrug candidates in cancer treatments: challenge and hope

“…More specifically, it binds to the catalytic site of the proteasome, preventing it from cleaving proteins. This leads to the accumulation of misfolded or damaged proteins within the cancer cell, which triggers a series of cellular events culminating in apoptosis 43 , 44 . This is important in myeloma cells because it involves inhibiting the proteasome complex and disrupting various cellular processes, ultimately leading to cancer cell death.…”

“…Ixazomib 2 has found to be even more potent and less likely to cause side effects. It does not only target CT-L, but also trypsin-like (T-L) and caspase-like (C-L) subunits 44 . Therefore, it is reported to have a higher selectivity and is usually given to patients who develop resistance to bortezomib 1 48 .…”

Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions

“…Specifically, the relatively weak C–B bonds (323 kJ mol −1 ) in BAs have played a major synthetic role as carbon nucleophiles ( Scheme 1 ). 2 For instance, the Suzuki–Miyaura coupling reaction, a “household” name in both academic and industrial settings, employed aryl halides and BAs to forge C–C bonds with high efficiency and great robustness. 3 Other transformations including Chan–Lam, 4 Matteson type 5 and Petasis reaction 6 have also been extensively investigated and advanced to applications.…”

Dual Nickel/Photoredox‐Catalyzed Site‐Selective Cross‐Coupling of 1,2‐Bis‐Boronic Esters Enabled by 1,2‐Boron Shifts

“…Organoboron compounds are some of the most valuable building blocks in organic synthesis because of the unique reactivity of CÀ B bonds. [1] A particularly powerful strategy in organoboron chemistry is the use of boron-selective reactions, wherein the reactants possess two or more boron moieties that exhibit different reactivities (Figure 1a), thus enabling the concise synthesis of complex molecules via multiple CÀ C bond-forming steps. [2] For example, boronselective Suzuki-Miyaura cross-couplings have been developed that employ a boronic acid protecting group, such as 1,8-diaminonaphthalene (DAN) or N-methyliminodiacetic acid (MIDA) ligands, which makes one of the boron moieties inactive towards transmetalation under palladium catalysis.…”