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  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylcarbamic acid esters

3-(Benzyloxycarbonylamino)-4-fluorophenylboronic Acid, Pinacol Ester

The compound 3-(Benzyloxycarbonylamino)-4-fluorophenylboronic Acid, Pinacol Ester (CAS No. 1256359-14-4) is a highly specialized intermediate in organic synthesis, particularly in the field of medicinal chemistry and materials science. This compound is notable for its unique structure, which combines a boronic acid group with a fluoro-substituted aromatic ring and a benzyloxycarbonyl (Cbz) protecting group. The presence of the pinacol ester further enhances its utility in cross-coupling reactions, making it a valuable tool in modern chemical synthesis.

The synthesis of 3-(Benzyloxycarbonylamino)-4-fluorophenylboronic Acid, Pinacol Ester typically involves multi-step processes that require precise control over reaction conditions to ensure high purity and yield. Recent advancements in catalytic methods and the use of environmentally friendly solvents have significantly improved the efficiency of its production. Researchers have also explored alternative routes to minimize by-products and optimize scalability, which is crucial for industrial applications.

In terms of applications, this compound has found extensive use in the construction of biologically active molecules. Its boronic acid functionality makes it an ideal substrate for Suzuki-Miyaura cross-coupling reactions, enabling the formation of diverse carbon-carbon bonds. The fluoro-substituted aromatic ring adds electronic diversity to the molecule, enhancing its potential as a building block in drug discovery programs targeting various therapeutic areas such as oncology and neurodegenerative diseases.

The integration of the benzyloxycarbonyl group provides additional versatility by allowing for controlled deprotection under mild conditions. This feature is particularly advantageous in multi-component synthesis strategies where sequential functionalization is required. Recent studies have demonstrated the successful incorporation of this compound into complex natural product syntheses, highlighting its role as a key intermediate in total synthesis efforts.

From a mechanistic perspective, the reactivity of 3-(Benzyloxycarbonylamino)-4-fluorophenylboronic Acid, Pinacol Ester has been extensively studied using computational chemistry tools. These investigations have provided insights into the electronic effects governing its reactivity in cross-coupling reactions. Such studies are essential for predicting reaction outcomes and optimizing synthetic pathways.

In conclusion, 3-(Benzyloxycarbonylamino)-4-fluorophenylboronic Acid, Pinacol Ester stands out as a versatile and powerful tool in contemporary organic synthesis. Its unique combination of functional groups and reactivity profiles makes it indispensable for constructing complex molecules with applications ranging from drug discovery to materials science. As research continues to uncover new synthetic methodologies and applications, this compound will undoubtedly remain at the forefront of chemical innovation.

• 508223-54-9(4-(Boc-Amino)-3-methylphenylboronic acid, pinacol ester)
• 363186-06-5(Benzyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate)
• 1351502-29-8(tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylmethylcarbamate)
• 1352413-09-2(tert-butyl N-[3-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate)
• 1218791-14-0(4-(Cbz-Amino)-3-fluorophenylboronic acid, pinacol ester)
• 1454682-73-5(prop-1-en-2-yl 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate)
• 262444-42-8(tert-butyl N-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate)
• 1218791-13-9(4-(Cbz-Amino)-2-fluorophenylboronic acid, pinacol ester)
• 1256256-45-7(tert-butyl N-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate)
• 1186637-38-6(tert-Butyl 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate)