Brian A. Keay

Synthesis of multi-substituted furan rings: the role of silicon

Silanes have proven extremely useful for the synthesis of multi-substituted furan rings. Their judicious placement on a furan ring can be used to control either the placement of new groups around the furan ring or the silane can be directly replaced via an ipso-substitution. This paper will briefly review the role silicon has played in the preparation of furan rings having a variety of substituent patterns.

9‐Boraanthracene Derivatives Stabilized by N‐Heterocyclic Carbenes

2009: A boraanthracene odyssey: General routes to boraanthracene derivatives--long proposed, but never observed--are disclosed, along with the structural and photophysical properties of these compounds and their remarkable reactivity towards oxygen.

Mild base mediated desilylation of various phenolic silyl ethers

Abstract A variety of phenolic silyl ethers are easily desilylated in good to excellent yields by treatment with 1.1 equivalents of K 2 CO 3 , and ethanol containing 5 equivalents of water.

2.08 – Furans and their Benzo Derivatives: Applications

2.08.2.1 Agrochemical Bioregulators 396 2.08.2.2 Fermentation and Bioindustrial Chemistry 400 2.08.2.3 Food and Feed Chemistry 401 2.08.2.4 Textiles and Fibers 402 2.08.2.5 Dyes and Photosensitizes 403 2.08.2.6 Cellulose, Lignin, Paper, and Other Wood Products 403 2.08.2.7 Industrial Organic Chemicals, Leather, Fats, and Waxes 405 2.08.2.8 Surface Active Agents and Detergents 405 2.08.2.9 Fossil Fuels, Derivatives, and Related Products 406 2.08.2.10 Essential Oils and Cosmetics 407 2.08.2.11 Pharmaceuticals 408 2.08.2.12 Miscellaneous 413

Synthesis and comparative characterization of 9-boraanthracene, 5-boranaphthacene, and 6-borapentacene stabilized by the H2IMes carbene.

A general procedure for the preparation of three N-heterocyclic carbene stabilized, boron-containing acenes (9-boraanthracene, 5-boranaphthacene, and 6-borapentacene) is presented. The key steps involve a transmetallation reaction between BCl(3) and an appropriate stannacyclic precursor, and the dehydrochlorination of the H(2)IMes adduct of the chloroborane product. Comparative structural, photophysical, and redox properties reveal narrow HOMO-LUMO gaps relative to the all-carbon acene analogues.

Furans and their Benzo Derivatives: Applications

This chapter provides an overview of literature from 1996 on the applications of various furan and benzofuran containing compounds. In addition to compounds that contain a furan or benzofuran ring the chapter includes various derivatives of these compounds that contain one oxygen atom within a five-membered ring, i.e., dihydro- and tetrahydrofuran ring, 2(5H)- and 3(2H)-furanones, five-membered anhydrides, isobenzofurans, dibenzofurans, benzofuranones, benzoanhydrides, polyarylfurans (and derivatives therefrom), and their hydro derivatives. Applications include pharmaceuticals, textiles and fibers, fossil fuels, dyes and photosensitizers, surface active agents and detergents, cellulose, lignin, paper and other wood products, leather, fats, waxes, essential oils, cosmetics, agrochemical bioregulators, pesticides, polymers, and polymer additives. Simple furan and benzofuran derivatives like tetrahydrofuran, maleic, succinic and phthalic anhydride, are not discussed in detail.

Synthesis, resolution and application of 2,2′-bis(di-2-furylphosphino)-1,1′-binaphthalene

Abstract A six step synthesis and resolution of (±)-2,2′-bis(di-2-furylphosphino)-1,1′-binaphthalene 4 (TetFuBINAP) is described along with its use in asymmetric inter- and intramolecular Heck reactions.

A palladium catalyzed cross-coupling between furylborates (generated in situ) and organohalides

Abstract 4-Lithio-2-(t-butyldimethylsilyl)-3-(lithioxymethyl)furan, when treated with 2 equivalents of trimethyl borate, smoothly underwent palladium catalyzed cross-coupling reactions with a variety of organohalides to provide 2,3,4-trisubstituted furans in good to excellent yields.

The 1,4 O→C silyl migrations of various 3-[(trialkylsilyl)oxymethyl]-furans and -thiophenes

Abstract Numerous 3-[(trialkylsilyl)oxymethyl]-furans and -thiophenes undergo a 1,4 O→C silyl migration when treated with n-BuLi/HMPA in THF or DME to produce 2-(trialkylsilyl)-3-(hydroxymethyl)-furans and -thiophenes in good yields.

A mild palladium(II) catalyzed desilylation of phenolic t-butyldimethylsilyl ethers

Abstract A variety of phenolic t -butyldimethylsilyl ethers are easily removed in good to excellent yields by treatment with 5 mol % PdCl 2 (CH 3 CN) 2 in refluxing acetone containing 5 equivalents of water.