Two-component boronic acid catalysis for increased reactivity in challenging Friedel–Crafts alkylations with deactivated benzylic alcohols

2019 ◽  
Vol 17 (24) ◽  
pp. 6007-6014 ◽  
Author(s):  
Hwee Ting Ang ◽  
Jason P. G. Rygus ◽  
Dennis G. Hall
Keyword(s):  
Boronic Acid ◽  
Acid Catalysis ◽  
Acid Catalyst ◽  
Co Catalyst ◽  
Benzylic Alcohols ◽  
Two Component

The combination of a boronic acid catalyst with perfluoropinacol as a co-catalyst improves the scope of Friedel–Crafts benzylations of arenes with electronically deactivated primary and secondary benzylic alcohols.

scholarly journals Recent Advances in Transition-Metal-Free (4+3)-Annulations

Synthesis ◽  
2021 ◽  
Author(s):  
Heather Lam ◽  
Mark Lautens ◽  
Xavier Abel-Snape ◽  
Martin F. Köllen
Keyword(s):  
Transition Metal ◽  
Boronic Acid ◽  
Lewis Acids ◽  
Acid Catalysis ◽  
Heterocyclic Carbenes ◽  
Bronsted Acids ◽  
Metal Free ◽  
Previous Review ◽  
Dual Activation ◽  
Metal Catalyzed

Abstract(4+3)-Annulations are incredibly versatile reactions which combine a 4-atom synthon and a 3-atom synthon to form both 7-membered carbocycles as well as heterocycles. We have previously reviewed transition-metal-catalyzed (4+3)-annulations. In this review, we will cover examples involving bases, NHCs, phosphines, Lewis and Brønsted acids as well as some rare examples of boronic acid catalysis and photocatalysis. In analogy to our previous review, we exclude annulations involving cyclic dienes like furan, pyrrole, cyclohexadiene or cyclopentadiene, as Chiu, Harmata, Fernándes and others have recently published reviews encompassing such substrates. We will however discuss the recent additions (2010–2020) to the literature on (4+3)-annulations involving other types of 4-atom-synthons.1 Introduction2 Bases3 Annulations Using N-Heterocyclic Carbenes3.1 N-Heterocyclic Carbenes (NHCs)3.2 N-Heterocyclic Carbenes and Base Dual-Activation4 Phosphines5 Acids5.1 Lewis Acids5.2 Brønsted Acids6 Boronic Acid Catalysis and Photocatalysis7 Conclusion

Development of chiral bisphosphoric acid/Boronic acid Co-catalyst system for enantioselective SN2’ reaction

Tetrahedron ◽  
2021 ◽  
pp. 132412
Author(s):  
Satavisha Kayal ◽  
Jun Kikuchi ◽  
Naoya Shinagawa ◽  
Shigenobu Umemiya ◽  
Masahiro Terada
Keyword(s):  
Boronic Acid ◽  
Catalyst System ◽  
Co Catalyst ◽  
Sn2 Reaction

Two-Component Optical Sugar Sensing Using Boronic Acid-Substituted Viologens with Anionic Fluorescent Dyes

2007 ◽  
pp. 47-87 ◽  
Author(s):  
David B. Cordes ◽  
Jeff T. Suri ◽  
Frank E. Cappuccio ◽  
Jason N. Camara ◽  
Soya Gamsey ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Fluorescent Dyes ◽  
Sugar Sensing ◽  
Two Component

Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides

Synlett ◽  
2019 ◽  
Vol 30 (14) ◽  
pp. 1679-1682 ◽  
Author(s):  
Yuta Otsuka ◽  
Yuto Shimazaki ◽  
Hitoshi Nagaoka ◽  
Keiji Maruoka ◽  
Takuya Hashimoto
Keyword(s):  
Carboxylic Acids ◽  
Asymmetric Catalysis ◽  
Acid Catalysis ◽  
Acid Catalyst ◽  
Oxidative Cyclization ◽  
Unsaturated Carboxylic Acids ◽  
Long Time ◽  
Scalable Synthesis ◽  
Enantioselective Catalysts

Chiral selenium π-acid catalysis has for a long time been lagging behind other areas of asymmetric catalysis due to a lack of highly enantioselective catalysts. In this regard, we recently developed the first chiral selenium π-acid catalyst which performs the oxidative cyclization of β,γ-unsaturated carboxylic acids with high enantioselectivities. We report herein our improved synthesis of this chiral selenium catalyst, which allows access to a large quantity of the catalyst as the diselenide. In addition, the catalyst is tested in the oxidative cyclization of N-methoxy β,γ-unsaturated amides to give iminolactones with high enantioselectivities.

Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75

2017 ◽  
Vol 53 (21) ◽  
pp. 3018-3021 ◽  
Author(s):  
Nobuya Nishi ◽  
Junki Nashida ◽  
Eisuke Kaji ◽  
Daisuke Takahashi ◽  
Kazunobu Toshima
Keyword(s):  
Boronic Acid ◽  
Acid Catalyst ◽  
E Coli

A novel regio- and stereoselective β-mannosylation using 1,2-anhydromannose and a diol sugar acceptor in the presence of a boronic acid catalyst and its application are reported.

ChemInform Abstract: Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo- and Heterocyclizations of Free Allylic Alcohols.

ChemInform ◽  
2012 ◽  
Vol 43 (45) ◽  
pp. no-no
Author(s):  
Hongchao Zheng ◽  
Sina Ghanbari ◽  
Shinji Nakamura ◽  
Dennis G. Hall
Keyword(s):  
Boronic Acid ◽  
Acid Catalysis ◽  
Allylic Alcohols
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