ASEAN Synergy to Overcome Challenges in Investment Arbitration

Cambodia, Indonesia, Lao, Malaysia, Thailand, and the Philippines, have been sued by foreign investors through International investment arbitrations (IIA). No matter whether the outcome is favorable or not, those countries have spend significant time, energy, and financial resources to arbitrate. ASEAN countries are not in advantageous position in IIA.The first and the most obvious reason is language barrier. Arbitration proceedins are mainly conducted in English. Consequently, the arbitrators and counsels more often than not come from English speaking countries. Not only do they lead to high cost, but also they lack of familiarity with South East Asia\u27s social, politics, economic, culture and customs. This may influence how they treat the cases such as the interpretation of provisions specifically designed to protect foreign investors such as: national treatment; fair and equitable treatment; most favored nation; and also in deciding jurisdictional issues. regional news as a legal basis for foreign investment activities aim to provide protection for foreign investor. On the other hand, it also serves as a mean to facilitate economic development in the host states of investment. Unfortunately, BITs often contain excessive and limitless protection clauses in order to attract foreign investors. This may endanger host states position as it can be used as a weapon by the investors to sue the host states. In responding to this fact, it is necessary to strengthen cooperation among ASEAN members in dealing with foreign investors through BIT. The ideal picture will be that SEA is pro-market and pro-arbitration reform. It is unavoidable that in order to protect themselves from harsh investors as well as intricate arbitration, ASEAN would be better off having its own investment arbitration center run by its experts. Thus, the short-term challenge is to equip legal practitioners, business players and academicians with more knowledge, skills and experiences in dealing with investment disputes. The long-term step will be to negotiate model of investment treaties applicable in the region and to harmonize national investment laws. These efforts are strategic opportunities for ASEAN as single market to keep balance between promoting investment, protecting investors and the host states at the same time

An <i>N</i>,<i>N</i>′-Diamidocarbene: Studies in C−H Insertion, Reversible Carbonylation, and Transition-Metal Coordination Chemistry

An N,N′-Diamidocarbene: Studies in C−H Insertion, Reversible Carbonylation, and Transition-Metal Coordination Chemistr

Increasing the Initiation Efficiency of Ruthenium-Based Ring-Opening Metathesis Initiators: Effect of Excess Phosphine

Increasing the Initiation Efficiency of Ruthenium-Based Ring-Opening Metathesis Initiators:  Effect of Excess Phosphin

An <i>N</i>,<i>N</i>′-Diamidocarbene: Studies in C−H Insertion, Reversible Carbonylation, and Transition-Metal Coordination Chemistry

An N,N′-Diamidocarbene: Studies in C−H Insertion, Reversible Carbonylation, and Transition-Metal Coordination Chemistr

Donor−Acceptor Triazenes: Synthesis, Characterization, and Study of Their Electronic and Thermal Properties

A new class of 1,3-disubstituted-triazenes were synthesized by coupling functionalized benzimidazol-2-ylidenes, as their free N-heterocyclic carbenes or generated in situ from their respective benzimidazolium precursors, to various aryl azides in modest to excellent isolated yields (36−99%). Electron delocalization between the two coupled components was studied using UV−vis spectroscopy, NMR spectroscopy, and X-ray crystallography. Depending on the complementarity of the functional groups on the N-heterocyclic carbenes and the organic azides, the respective triazenes were found to exhibit λmax values ranging between 364 and 450 nm. X-ray crystallography revealed bond alteration patterns in a series of triazenes characteristic of donor−acceptor compounds. Triazene thermal stabilities were studied using thermogravimetric analysis and found to be strongly dependent on the sterics of the benzimidazol-2-ylidene component and the electronics of the azide component. Triazenes possessing bulky N-substituents (e.g., neo-pentyl, tert-butyl, etc.) were stable in the solid-state to temperatures exceeding 150 °C, whereas analogues with small N-substituents (e.g., methyl) were found to slowly decompose at room temperature. Triazenes featuring electron-rich phenyl azide components decomposed at higher temperatures than their electron-deficient analogues. Products of the thermally induced triazene decomposition reaction were identified as molecular nitrogen and the respective guanidine. Using an isotopically labeled triazene, the mechanism of the decomposition reaction was found to be analogous to the Staudinger reaction

Olefin Metathesis Catalysts Containing <i>N,N′</i>-Diamidocarbenes

A series of Ru-based olefin metathesis catalysts containing N,N′-diamidocarbenes (DACs) were synthesized and studied. X-ray crystallographic analysis revealed that the Ru−Ccarbene distances (1.938(5)−1.984(4) Å) measured in the DAC-supported complexes were relatively short, particularly in comparison to the range of Ru−Ccarbene distances typically observed in analogous N-heterocyclic carbene (NHC) supported complexes (1.96−2.03 Å). While the Tolman electronic parameters (TEP) of various DACs (2056−2057 cm−1) were calculated to be similar to that of PCy3 (2056 cm−1), the ring-closing metathesis (RCM) of diethyl diallylmalonate facilitated by DAC-supported Ru complexes proceeded at a relatively slow rate. However, unlike the phosphine-containing complexes, the DAC analogues catalyzed the RCM of diethyl dimethallylmalonate to its respective tetrasubstituted olefin. A series of electrochemical experiments revealed that the Ru complexes bearing a DAC ligand underwent oxidation at significantly higher potentials (ΔEpa > 0.5 V) than analogous complexes containing phosphines and various N-heterocyclic carbenes (NHCs), including a tetrahydropyrimidinylidene, a saturated and strongly donating NHC analogue of the DAC. The relative catalytic activities observed were attributed to the steric properties of the aforementioned ligands

Alkyne and Reversible Nitrile Activation: <i>N</i>,<i>N</i>′-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines

We report the synthesis of a variety of diamidocyclopropenes by combining an isolable and readily accessible N,N′-diamidocarbene (DAC) with a range of alkynes (nine examples, 68–97% yield). Subsequent hydrolysis of selected cyclopropenes afforded the corresponding cyclopropenones or α,β-unsaturated acids, depending on the reaction conditions. In addition, the combination of a DAC with alkyl or aryl nitriles was found to form 2H-azirines in a reversible manner (four examples, Keq = 4–72 M–1 at 30 °C in toluene)

Structurally Dynamic Materials Based on Bis(<i>N</i>-heterocyclic carbene)s and Bis(isothiocyanate)s: Toward Reversible, Conjugated Polymers

Structurally Dynamic Materials Based on Bis(N-heterocyclic carbene)s and Bis(isothiocyanate)s: Toward Reversible, Conjugated Polymer

Donor−Acceptor Triazenes: Synthesis, Characterization, and Study of Their Electronic and Thermal Properties

A new class of 1,3-disubstituted-triazenes were synthesized by coupling functionalized benzimidazol-2-ylidenes, as their free N-heterocyclic carbenes or generated in situ from their respective benzimidazolium precursors, to various aryl azides in modest to excellent isolated yields (36−99%). Electron delocalization between the two coupled components was studied using UV−vis spectroscopy, NMR spectroscopy, and X-ray crystallography. Depending on the complementarity of the functional groups on the N-heterocyclic carbenes and the organic azides, the respective triazenes were found to exhibit λmax values ranging between 364 and 450 nm. X-ray crystallography revealed bond alteration patterns in a series of triazenes characteristic of donor−acceptor compounds. Triazene thermal stabilities were studied using thermogravimetric analysis and found to be strongly dependent on the sterics of the benzimidazol-2-ylidene component and the electronics of the azide component. Triazenes possessing bulky N-substituents (e.g., neo-pentyl, tert-butyl, etc.) were stable in the solid-state to temperatures exceeding 150 °C, whereas analogues with small N-substituents (e.g., methyl) were found to slowly decompose at room temperature. Triazenes featuring electron-rich phenyl azide components decomposed at higher temperatures than their electron-deficient analogues. Products of the thermally induced triazene decomposition reaction were identified as molecular nitrogen and the respective guanidine. Using an isotopically labeled triazene, the mechanism of the decomposition reaction was found to be analogous to the Staudinger reaction

Olefin Metathesis Catalysts Containing <i>N,N′</i>-Diamidocarbenes

A series of Ru-based olefin metathesis catalysts containing N,N′-diamidocarbenes (DACs) were synthesized and studied. X-ray crystallographic analysis revealed that the Ru−Ccarbene distances (1.938(5)−1.984(4) Å) measured in the DAC-supported complexes were relatively short, particularly in comparison to the range of Ru−Ccarbene distances typically observed in analogous N-heterocyclic carbene (NHC) supported complexes (1.96−2.03 Å). While the Tolman electronic parameters (TEP) of various DACs (2056−2057 cm−1) were calculated to be similar to that of PCy3 (2056 cm−1), the ring-closing metathesis (RCM) of diethyl diallylmalonate facilitated by DAC-supported Ru complexes proceeded at a relatively slow rate. However, unlike the phosphine-containing complexes, the DAC analogues catalyzed the RCM of diethyl dimethallylmalonate to its respective tetrasubstituted olefin. A series of electrochemical experiments revealed that the Ru complexes bearing a DAC ligand underwent oxidation at significantly higher potentials (ΔEpa > 0.5 V) than analogous complexes containing phosphines and various N-heterocyclic carbenes (NHCs), including a tetrahydropyrimidinylidene, a saturated and strongly donating NHC analogue of the DAC. The relative catalytic activities observed were attributed to the steric properties of the aforementioned ligands