scholarly journals meta-Selective C–H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester

2020 ◽  
Vol 11 (12) ◽  
pp. 3301-3306 ◽  
Author(s):  
Alexander F. Williams ◽  
Andrew J. P. White ◽  
Alan C. Spivey ◽  
Christopher J. Cordier
Keyword(s):  
Acid Derivative ◽  
Boronic Acids ◽  
Protecting Group ◽  
Boronate Ester ◽  
Methyliminodiacetic Acid

An N-methyliminodiacetic acid derivative allows the meta-C–H functionalisation of boronic acids, acting simultaneously as a directing and protecting group.

scholarly journals Vibrational Spectroscopy of N-Methyliminodiacetic Acid (MIDA)-Protected Boronate Ester: Examination of the B–N Dative Bond

2011 ◽  
Vol 115 (24) ◽  
pp. 6426-6431 ◽  
Author(s):  
Dana N. Reinemann ◽  
Ashley M. Wright ◽  
Jonathan D. Wolfe ◽  
Gregory S. Tschumper ◽  
Nathan I. Hammer
Keyword(s):  
Vibrational Spectroscopy ◽  
Boronate Ester ◽  
Dative Bond ◽  
Methyliminodiacetic Acid

scholarly journals On the rate of boronate ester formation inortho-aminomethyl-functionalised phenyl boronic acids

2013 ◽  
Vol 25 (2) ◽  
pp. 79-86 ◽  
Author(s):  
Byron E. Collins ◽  
Pedro Metola ◽  
Eric V. Anslyn
Keyword(s):  
Boronic Acids ◽  
Boronate Ester ◽  
Ester Formation

(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates

2012 ◽  
Vol 84 (11) ◽  
pp. 2339-2416 ◽  
Author(s):  
C. Annette Berg ◽  
Nils C. Eichenauer ◽  
Jörg Pietruszka
Keyword(s):  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Boronic Acids ◽  
Protecting Group ◽  
Enantiomerically Pure

Tartrate-derived (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol has found diverse applications in asymmetric organic synthesis. Among these, its utilization as a protecting group for boronic acids has been investigated extensively. Besides being extraordinarily stable and thus allowing a plethora of transformations, it enables access to various diastereo- and enantiomerically pure organoboron reagents and versatile intermediates in asymmetric synthesis.

A novel redox-sensitive protecting group for boronic acids, MPMP-diol

2005 ◽  
Vol 46 (49) ◽  
pp. 8503-8505 ◽  
Author(s):  
Jun Yan ◽  
Shan Jin ◽  
Binghe Wang
Keyword(s):  
Boronic Acids ◽  
Protecting Group

Efficient Synthesis of Bicyclic Peptide BI-32169 Utilizing a Novel Aryl Boronate Ester Protecting Group

2018 ◽  
Vol 76 (2) ◽  
pp. 95
Author(s):  
Hui Song ◽  
Chao Liu ◽  
Yijun Wu ◽  
Honggang Hu ◽  
Fang Yan
Keyword(s):  
Protecting Group ◽  
Efficient Synthesis ◽  
Boronate Ester

scholarly journals Cyclopentadithiophene polymers synthesised via Suzuki-Miyaura polymerisation of MIDA boronate esters

2020 ◽  
Vol 1 ◽  
Author(s):  
Josue Ayuso-Carrillo
Keyword(s):  
Conjugated Polymers ◽  
Organic Electronics ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Boronate Esters ◽  
Boronate Ester ◽  
Cross Coupling Reaction ◽  
Synthetic Routes ◽  
Methyliminodiacetic Acid

AbstractCyclopentadithiophene (CPDT), a Csp3-bridged bithiophene heteroaromatic unit, displays interesting properties when it is embedded in the repeating units of π-conjugated polymers, and they are applied in organic electronics devices. Common synthetic routes to CPDT-derived polymers rely on toxic methodologies whilst alternative non-toxic strategies such as the Suzuki-Miyaura reaction have been less studied. In this report we demonstrate that the use of a N-methyliminodiacetic acid (MIDA) boronate ester-derived CPDT monomer allows the efficient formation of poly(cyclopentadithiophene) homopolymer under Suzuki-Miyaura cross-coupling reaction conditions. Thus, the use of MIDA boronate esters might be extended to other organic units to design and construct a plethora of π-conjugated polymers.

A Novel Redox-Sensitive Protecting Group for Boronic Acids, MPMP-Diol.

ChemInform ◽  
2006 ◽  
Vol 37 (12) ◽  
Author(s):  
Jun Yan ◽  
Shan Jin ◽  
Binghe Wang
Keyword(s):  
Boronic Acids ◽  
Protecting Group
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