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2004
Carboxylic acid esters
Q 0530
Rhodium-Catalyzed Heck-Type Coupling of Boronic Acids with Activated Alkin an Aqueous Emulsion. — The coupling reaction between arylboronic acids
51- 073 enes
and activated alkenes catalyzed by a water-soluble tert-butyl amphos-rhodium complex
is found to progress at room temperature and generates Heck-type products (III) with
high yields and excellent selectivity. Steric hindrance around the boronic acid, cf. (Ib),
or substitution on the alkene, cf. (VI), encourages the formation of products arising
from a conjugate addition-protonation process. In the case of Heck product formation,
it is necessary to add two equivalents of the alkene component whereby one equivalent
is believed to act as a sacrificial hydride acceptor. — (LAUTENS*, M.; MANCUSO,
J.; GROVER, H.; Synthesis 2004, 12, 2006-2014; Davenport Res. Lab., Dep. Chem.,
Univ. Toronto, Toronto, Ont. M5S 3H6, Can.; Eng.) — Bartels
2004
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