Special Issue "Heck Coupling"

Guest Editor
Prof. Dr. Cinzia Chiappe
Dipartimento di Chimica e Chimica Industriale, University of Pisa, c/o via Bonanno 33, 56126 Pisa, Italy
E-Mail:
Interests: Pd promoted cross couplings, regioselectivity of inter- and intramolecular reactions, catalyst developments, neoteric solvents, Heck reactions in solid phases, continuous processes, waste-minimized processes

Submission

All papers should be submitted to molecules@mdpi.org with copy to the guest editor. To be published continuously until the deadline and papers will be listed together at the special websites.

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• Pd promoted cross couplings
• Regioselectivity of inter- and intramolecular reactions
• Catalyst developments
• Neoteric solvents
• Heck reactions in solid phases
• Continuous processes
• Waste-minimized processes

Manuscript ID: Molecules-heckcp-20090717-Chiappe-it
Type of Paper: Review
Title: The Heck Reaction in Ionic Liquids: Progress and Challenges
Authors: Cinzia Chiappe and Fabio Bellina
Affiliation: Dipartimento di Chimica e Chimica Industriale, via Risorgimento 35, 56126 Pisa, Italy; Email: cinziac@farm.unipi.it
Abstract: As the interest for environmental increases and environmental laws become more stringent, the need to replace existing processes with new more sustainable technologies becomes a primary objective. The use of ionic liquids to replace organic solvents in metal catalyzed reactions has recently gained much attention and great progress has been accomplished in this area in the last years. This paper reviews the recent developments in the application of ionic liquids and related systems (supported ionic liquids, ionic polymers, and so on) in the Heck reaction. Merits and achievements of ionic liquids were analyzed and discussed considering the possibility of increasing the effectiveness of industrial processes.

Type of Paper: Review
Title: The Heck Coupling in Peptide Science
Author: Gerardo Byk
Affiliation: Laboratory of Nano-Biotechnology Dept. of Chemistry Bar-Ilan University 52900-Ramat Gan ISRAEL; Email: bykger@mail.biu.ac.il
Abstract: The use of Heck coupling has been extensively applied to small molecules synthesis but unlike ring-closure metathesis (Grubbs) reaction only at a limited extent to peptide chemistry for peptide decoration and some peptide cyclization. We acknowledge 62 citations in scifinder using the keywords "Heck reaction" and "peptide" , while when using "Metathesis" and "peptide" we find at least 576 results. The main reason that hampered the use of this reaction in peptide science is the strong conditions needed in many cases for obtaining the products in contrast to Grubbs metathesis. This reaction is usually carried out over 120 0C for long period of times even several days especially when difficult cyclization is needed. The use of microwave energy facilitated dramatically the use of this reaction in peptide science. We will report a comprehensive review going from the early use of Heck coupling in peptide science until the late applications using microwave assisted Heck coupling in peptides and potential future applications both in solution and solid phase. The aim of the review will be to motivate chemists in peptide science to improve the use of this reaction for peptidomimetic and other modifications needed in peptide science.

Manuscript ID: Molecules-heckcp-20090804-Lee-kr
Type of Paper: Review
Title: Palladium Catalyzed Heck Coupling Reactions Using Phosphite Ligand
Authors: Eunhye Jung and Sunwoo Lee
Affiliation: Department of Chemistry, Chonnam National University, 300 Yongbong-dong, Buk-gu, Gwangju 500-757, Republic of Korea; Email: sunwoo@chonnam.ac.kr
Abstract: The catalystic system based on palladium-phosphite for Heck coupling reactions of aryl halides and olefins is described. The palladium-phosphite catalyst effectively promotes Heck reactions of aryl halides to give the desired products in moderate to excellent yields.

Manuscript ID: Molecules-heckcp-20090806-Deagostino-it
Type of Paper: Review
Title: The Heck reaction applied to 1,3- and 1,2-Unsaturated Derivatives, a way toward molecular targets.
Authors: Annamaria Deagostino, Cristina Prandi, Paolo Venturello
Affiliation: Dipartimento di Chimica Generale e Chimica Organica dell’Università di Torino Via Pietro Giuria, 7 - 10125 Torino , Italy; Emails: annamaria.deagostino@unito.it, paolo.venturello@unito.it, cristina.prandi@unito.it
Abstract: This review will deal with the recent developments in the Heck coupling of 1,3- and 1,2 dienic systems. Both these system show a particular reactivity in Pd(0) cross coupling reactions because they form a π-allylic palladium complexe. This complex can also react with nucleophiles in inter- and intramolecular manner, affording many different structures.
In particular, the use of these derivatives to achieve structures correlated to biologically active compounds and domino processes will be described. Moreover our recent studies concerning the synthesis of γ-arylated α,β-unsaturated carbonyl compounds, by regioselective Heck process on 1-alkoxy-1,3-dienes in ionic liquids will be reviewed, in conjunction with the Heck coupling of 1,2-dien-1-ols to α-arylated α,β-unsaturated aldehydes.

Manuscript ID: Molecules-heckcp-20090911-Goossen-de
Type of Paper: Article
Title: Pd-Catalyzed Decarboxylative Heck Vinylation of 2-nitrobenzoates in the Presence of CuF₂
Authors: Lukas J. Goossen and Bettina Zimmermann; E-Mails: goossen@chemie.uni-kl.de, zimmermann@chemie.uni-kl.de
Abstract: A new protocol for the decarboxylative Heck vinylation of benzoic acids is disclosed. In the presence of a catalyst system generated in situ from Pd(OAc)₂ (2 mol%), CuF₂ (2 equiv), and benzoquinone (0.5 equiv) in NMP, a wide range of olefins were coupled with various 2-nitrobenzoates at 130 °C under release of carbon dioxide, affording the corresponding vinyl arenes in good yields.