TY - JOUR
T1 - Desymmetrization of Diboron(4) by a Trifluorination B-Masking Strategy
T2 - Practical Synthesis of Unsymmetrical Diboron Species
AU - Eghbarieh, Nadim
AU - Masarwa, Ahmad
N1 - Publisher Copyright:
© 2024 The Authors. Published by American Chemical Society.
PY - 2024/8/16
Y1 - 2024/8/16
N2 - Herein, we report a straightforward practical and simple method for efficiently synthesizing a BF3-containing unsymmetrical diboron salt. This method involves the direct desymmetrization of commercially available diboron(4). This desymmetrization is based on a selective B-masking strategy via nucleophilic trifluorination, providing the elusive diborons bearing a trifluoroborate group. The synthetic utility of these salts is demonstrated through various examples of (sequential) B-ligand interconversions, enabling the synthesis of unsymmetrical diboron derivatives. These products, which serve as valuable building blocks, are obtained in gram-scale and high yields.
AB - Herein, we report a straightforward practical and simple method for efficiently synthesizing a BF3-containing unsymmetrical diboron salt. This method involves the direct desymmetrization of commercially available diboron(4). This desymmetrization is based on a selective B-masking strategy via nucleophilic trifluorination, providing the elusive diborons bearing a trifluoroborate group. The synthetic utility of these salts is demonstrated through various examples of (sequential) B-ligand interconversions, enabling the synthesis of unsymmetrical diboron derivatives. These products, which serve as valuable building blocks, are obtained in gram-scale and high yields.
UR - http://www.scopus.com/inward/record.url?scp=85200369981&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.4c00715
DO - 10.1021/acs.joc.4c00715
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C2 - 39086151
AN - SCOPUS:85200369981
SN - 0022-3263
VL - 89
SP - 11753
EP - 11760
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -