TY - JOUR
T1 - Light-Induced Gold-Catalyzed Hiyama Arylation
T2 - A Coupling Access to Biarylboronates
AU - Xie, Jin
AU - Sekine, Kohei
AU - Witzel, Sina
AU - Krämer, Petra
AU - Rudolph, Matthias
AU - Rominger, Frank
AU - Hashmi, A. Stephen K.
N1 - Funding Information:
Jin Xie gratefully acknowledges National Natural Science Foundation of China (21702098), “1000-Youth Talents Plan” as well as the Fundamental Research Funds for the Central Universities (No. 020514380158) and Sina Witzel is grateful for the support by the Landesgraduiertenfçrderung of the state of Baden-Württemberg, Germany.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/12/17
Y1 - 2018/12/17
N2 - Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C−X (heteroatom) and C−C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.
AB - Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C−X (heteroatom) and C−C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.
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U2 - 10.1002/anie.201806427
DO - 10.1002/anie.201806427
M3 - Article
C2 - 30300942
AN - SCOPUS:85056748979
SN - 1433-7851
VL - 57
SP - 16648
EP - 16653
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 51
ER -