Pincer Carbene Enables Nitrile Coupling

Pincer Carbene Enables Nitrile Coupling

Pincer carbene ligands mediate the coupling of a coordinated acetonitrile ligand and its unusual reactivity opens application in catalysis

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A Short, Gram-Scale Synthesis of 2,5-Disubstituted Furans

A Short, Gram-Scale Synthesis of 2,5-Disubstituted Furans (pages 3219–3222)
Stanley Chang, Saheena Desai, Daniel B. Leznoff, Nabyl Merbouh and Robert Britton
 | DOI: 10.1002/ejoc.201300305

European Journal of Organic Chemistry

A modified Feist–Bénary furan synthesis has been developed that involves a lithium aldol reaction of an -chloroaldehyde followed by a thermally induced tetrahydrofuran formation/dehydration sequence. This process provides access to a range of 2,5-disubstituted furans and is demonstrated on multigram scale.

A modified Feist–Bénary furan synthesis has been developed that involves a lithium aldol reaction between a methyl ketone and an α-chloroaldehyde followed by a thermally induced tetrahydrofuran formation/dehydration sequence and affords 2,5-disubstituted furans in good overall yield. This process is demonstrated on multigram scale and is amenable to the production of symmetric or asymmetric furans that incorporate a range of substituents (e.g., aryl, tert-butyl, ferrocenyl).

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300305/abstract

Large-Scale Carbonyl Reductions in the Pharmaceutical Industry

Abstract Image

discuss the most common and reliable methods for the reduction of aldehydes, ketones, carboxylic acids, esters, amides, imides, and acid chlorides. Representative examples illustrate detailed reaction and workup conditions and highlight the advantages and limitations of each reducing agent with special emphasis on safety, cost, and amenability to scale-up.

Review

Large-Scale Carbonyl Reductions in the Pharmaceutical Industry

Chemical Research and Development, Pharmaceutical Sciences, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, United States
Org. Process Res. Dev., 2012, 16 (6), pp 1156–1184
DOI: 10.1021/op2003826
Publication Date (Web): February 14, 2012
Herein the authors  present a review on methods for carbonyl reductions on large scale (≥100 mmol) applied to the synthesis of drug candidates in the pharmaceutical industry. We discuss the most common and reliable methods for the reduction of aldehydes, ketones, carboxylic acids, esters, amides, imides, and acid chlorides. Representative examples illustrate detailed reaction and workup conditions and highlight the advantages and limitations of each reducing agent with special emphasis on safety, cost, and amenability to scale-up.

Synthon identification in co-crystals and polymorphs with IR spectroscopy. Primary amides as a case study

Synthon identification in co-crystals and polymorphs with IR spectroscopy. Primary amides as a case study

CrystEngComm, 2013, Advance Article
DOI: 10.1039/C3CE40286J, Paper
Arijit Mukherjee, Srinu Tothadi, Shaunak Chakraborty, Somnath Ganguly, Gautam R. Desiraju
IR marker bands are used to identify multiple synthons in polymorphs and co-crystals

IR spectroscopy has been widely employed to distinguish between different crystal forms such as polymorphs, clathrates, hydrates and co-crystals. IR has been used to monitor co-crystal formation and single synthon detection. In this work, we have developed a strategy to identify multiple supramolecular synthons in polymorphs and co-crystals with this technique.

The identification of multiple synthons in co-crystals with IR is difficult for several reasons. In this paper, a four step method involving well assigned IR spectral markers that correspond to bonds in a synthon is used. IR spectra of three forms of the co-crystal system, 4-hydroxybenzoic acid:4,4′-bipyridine (2 : 1), show clear differences that may be attributed to differences in the synthon combinations existing in the forms (synthon polymorphism).

These differences were picked out from the three IR spectra and the bands analysed and assigned to synthons. Our method first identifies IR marker bands corresponding to (covalent) bonds in known/model crystals and then the markers are mapped in known co-crystals having single synthons. Thereafter, the IR markers are queried in known co-crystals with multiple synthons.

Finally they are queried in unknown co-crystals with multiple synthons. In the last part of the study, the N–H stretching absorptions of primary amides that crystallize with the amide dimers linked in a ladder like chain show two specific absorptions which are used as marker absorptions and all variations of this band structure have been used to provide details on the environment around the dimer. The extended dimer can accordingly be easily distinguished from the isolated dimer.

CrystEngComm, 2013, Advance Article

Arijit mukherjee et al
DOI: 10.1039/C3CE40286J
Received 14 Feb 2013, Accepted 28 Mar 2013
First published online 02 Apr 2013

link

http://pubs.rsc.org/en/Content/ArticleLanding/2013/CE/C3CE40286J?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FCE+%28RSC+-+CrystEngComm+latest+articles%29