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Peter Langer - One of the best experts on this subject based on the ideXlab platform.
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Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C–N coupling and C–H activation reactions
Organic & biomolecular chemistry, 2014Co-Authors: Tran Quang Hung, Alexander Villinger, Ngo Ngoc Thang, Huy Hoang, Tuan Thanh Dang, Peter LangerAbstract:A new and efficient strategy for the synthesis of 3,9′- and 2,9′-biscarbazoles was developed. Our strategy relies on the cyclization of 1,1′-biphenyl-2,2′-diyl bis(trifluoromethanesulfonate) with 4- or 3-anisidine, transformation of the methoxy to a Triflate Group and subsequent oxidative Pd-catalyzed cyclization with various anilines.
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Chemoselective Suzuki–Miyaura cross-coupling reactions of methyl 4-bromo-3-(trifluoromethylsulfonyloxy)-2-naphthoate
Tetrahedron Letters, 2013Co-Authors: Zien Khaddour, Alexander Villinger, Nadi Eleya, Omer A. Akrawi, Aws M. Hamdy, Tamás Patonay, Peter LangerAbstract:Arylated naphthalenes were prepared by Suzuki–Miyaura cross-coupling reactions of methyl 4-bromo-3-(trifluoromethylsulfonyloxy)-2-naphthoate. The reactions proceeded with very good chemoselectivity in favor of the Triflate Group, due to additive electronic ortho electronic effects.
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synthesis of aryl substituted naphthalenes by chemoselective suzuki miyaura reactions of bromo trifluoromethanesulfonyloxy naphthalenes influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
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Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
Alexander Villinger - One of the best experts on this subject based on the ideXlab platform.
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Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C–N coupling and C–H activation reactions
Organic & biomolecular chemistry, 2014Co-Authors: Tran Quang Hung, Alexander Villinger, Ngo Ngoc Thang, Huy Hoang, Tuan Thanh Dang, Peter LangerAbstract:A new and efficient strategy for the synthesis of 3,9′- and 2,9′-biscarbazoles was developed. Our strategy relies on the cyclization of 1,1′-biphenyl-2,2′-diyl bis(trifluoromethanesulfonate) with 4- or 3-anisidine, transformation of the methoxy to a Triflate Group and subsequent oxidative Pd-catalyzed cyclization with various anilines.
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Chemoselective Suzuki–Miyaura cross-coupling reactions of methyl 4-bromo-3-(trifluoromethylsulfonyloxy)-2-naphthoate
Tetrahedron Letters, 2013Co-Authors: Zien Khaddour, Alexander Villinger, Nadi Eleya, Omer A. Akrawi, Aws M. Hamdy, Tamás Patonay, Peter LangerAbstract:Arylated naphthalenes were prepared by Suzuki–Miyaura cross-coupling reactions of methyl 4-bromo-3-(trifluoromethylsulfonyloxy)-2-naphthoate. The reactions proceeded with very good chemoselectivity in favor of the Triflate Group, due to additive electronic ortho electronic effects.
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synthesis of aryl substituted naphthalenes by chemoselective suzuki miyaura reactions of bromo trifluoromethanesulfonyloxy naphthalenes influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
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Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
Zahid Hassan - One of the best experts on this subject based on the ideXlab platform.
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synthesis of aryl substituted naphthalenes by chemoselective suzuki miyaura reactions of bromo trifluoromethanesulfonyloxy naphthalenes influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
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Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
Munawar Hussain - One of the best experts on this subject based on the ideXlab platform.
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synthesis of aryl substituted naphthalenes by chemoselective suzuki miyaura reactions of bromo trifluoromethanesulfonyloxy naphthalenes influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
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Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters
Tetrahedron, 2012Co-Authors: Zahid Hassan, Alexander Villinger, Munawar Hussain, Peter LangerAbstract:Chemoselective Suzuki–Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the Triflate Group is electronically more deficient by the presence of a neighbouring acetyl Group.
Christopher P. Holmes - One of the best experts on this subject based on the ideXlab platform.
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The Traceless Solid-Phase Synthesis of Organic Molecules
Methods in enzymology, 2003Co-Authors: David Tumelty, Yijun Pan, Christopher P. HolmesAbstract:Publisher Summary This chapter discusses two approaches that illustrate different tactics used in the goal of synthesizing organic compounds in a traceless manner. In the first strategy, a linker and a scaffold combine synergistically to achieve a traceless synthesis of diverse substituted benzimidazole compounds and libraries. The traceless synthetic route to create such libraries delivers compounds in moderate yields but in high purity directly after cleavage from the solid support. In the second strategy, a novel linker is used in a more global fashion to synthesize target compounds by activation of chemically diverse phenols. The strategy is based on the well-known activation properties of Triflates (trifluoromethanesulfonyls) that are widely used as precursors for aryl and vinyl cations due to their excellent leaving Group properties. Once an oxygen atom on the phenol moiety is activated by the Triflate Group, it becomes possible to carry out a reductive cleavage (deoxygenating the phenol) or cross-coupling reactions. This gives rise to a variety of substituted aromatics, or olefins at the “inert” phenolic or vinyl oxygen position.
