Highlights on the General Preference for Multi-Over Mono-Coupling in the Suzuki-Miyaura Reaction

被引：0
作者：
Lima, Carlos F. R. A. C. [1 ]
Lima, Marco A. L. [2 ]
Pinto, J. Ricardo M. [3 ]
Ribeiro, M. Gabriela T. C. [3 ]
Silva, Artur M. S. [4 ]
Santos, Luis M. N. B. F. [1 ]
机构：
[1] Univ Porto, Inst Mol Sci IMS, Dept Quim & Bioquim, CIQUP,Fac Ciencias, P-4169007 Porto, Portugal
[2] Univ Ulm, Inst Anorgan Chem 1, Albert Einstein Allee 11, D-89081 Ulm, Germany
[3] Univ Porto, Fac Sci, Dept Chem & Biochem, LAQV REQUIMTE, Rua Campo Alegre S-N, P-4169007 Porto, Portugal
[4] Univ Aveiro, Dept Chem, LAQV REQUIMTE, Campus Univ Santiago, P-3810193 Aveiro, Portugal
来源：
CATALYSTS | 2023年 / 13卷 / 06期
关键词：
oxidative addition; organocatalysis; Pd catalyst; multi-coupling; reaction selectivity; LIGAND-FREE SUZUKI; OXIDATIVE ADDITION; CONJUGATED POLYMERS; PRECISION SYNTHESIS; HETEROARYL HALIDES; HIGHLY EFFICIENT; CHAIN-GROWTH; CATALYST; POLYMERIZATION; MECHANISMS;
D O I：
10.3390/catal13060928
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A systematic synthetic study was performed to explain the usual trend in selectivity towards multi-coupling, over mono-coupling, in Suzuki-Miyaura reactions. This preference was observed under different reaction conditions: for various halobenzenes, using substituents on the boronic acid, and changing the catalyst and temperature. Moreover, this reaction selectivity was found to increase for more reactive systems towards oxidative addition and more diluted media. The results constitute experimental evidence that the formation of the totally substituted coupling product is kinetically favoured by a reaction path location-the proximity between the regenerated catalyst and the newly formed coupling intermediate promotes the subsequent reaction.
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页数：12
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