Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 21, Pages 5806-5811Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201702107
Keywords
chiral anions; Heck-Matsuda reaction; Heck reaction; palladium; phase-transfer catalysis
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Funding
- National Institute of General Medical Sciences [R35 GM118190, R01 GM063540]
- Science without Borders [CSF/CNPq 201758/2014-8]
- UNCF
- Merck
- NIH Shared Instrumentation Grant [S10-RR027172]
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A mild, asymmetric Heck-Matsuda reaction of five-, six- and seven-membered ring alkenes and aryl diazonium salts is presented. High yields and enantioselectivities were achieved using Pd-0 and chiral anion co-catalysts, the latter functioning as a chiral anion phase-transfer (CAPT) reagent. For certain substrate classes, the chiral anion catalysts were modulated to minimize the formation of undesired by-products. More specifically, BINAM-derived phosphoric acid catalysts were shown to prevent alkene isomerization in cyclopentene and cycloheptene starting materials. DFT(B3LYP-D3) computations revealed that increased product selectivity resulted from a chiral anion dependent lowering of the activation barrier for the desired pathway.
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