Multistep Synthesis of Complex Boronic Acids from Simple MIDA Boronates
نویسندگان
چکیده
منابع مشابه
Multistep synthesis of complex boronic acids from simple MIDA boronates.
Due to its sensitivity to most synthetic reagents, it is typically necessary to introduce the boronic acid functional group just prior to its utilization. Overcoming this important limitation, we herein report that air- and chromatographically stable MIDA boronates are compatible with a wide range of common reagents which enables the multistep synthesis of complex boronic acid building blocks f...
متن کاملA general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.
Many boronic acids, including 2-heterocyclic, vinyl, and cyclopropyl derivatives, are inherently unstable, which can limit their benchtop storage and/or efficient cross-coupling. We herein report the first general solution to this problem: in situ slow release of unstable boronic acids from the corresponding air-stable MIDA boronates. This remarkably general approach has transformed all three c...
متن کاملTandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.
A tandem gold-catalyzed cycloisomerization/Suzuki cross coupling sequence involving arylethynyl-N-methyliminodiacetic acid boronates is described. Combining the mildness of homogeneous gold catalysis with the versatility of N-methyliminodiacetic acid (MIDA) boronates, this tandem two-step method enables the rapid assembly of various aryl-substituted heterocycles without having to isolate or pur...
متن کاملDimeric Boronates Derived from the Reaction of Schiff Bases and Boronic Acids
A síntese one-pot de complexos diméricos de boro é descrita. Os compostos foram obtidos pela reação de bases de Schiff (ligantes tridentados) com ácido trans-β-fenilvinilborônico, ácido 3tiofeninoborônico e ácido metilborônico. A construção das estruturas diméricas é favorecida pela presença de ligações de coordenação N→B intramoleculares, resultando na formação de anéis heterociclicos de dez m...
متن کاملRegioselective routes to orthogonally-substituted aromatic MIDA boronates.
A series of tetrasubstituted aromatics has been synthesized, many of which are based on elaborated N-methyliminodiacetic acid (MIDA)-boronates. A sequence employing nitration, bromination, stepwise Suzuki-Miyaura (SM) coupling with a boronic acid, then base-mediated unmasking of the boronic acid from the MIDA-boronate and a second SM-coupling has led to our desired, mainly 1,2,4,5-substituted t...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2008
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja8063759