Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures
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- Shin Ando
- Faculty of Life Sciences, Kumamoto University, 5-1 Oe-honmachi Chuo-ku, Kumamoto 862-0973, Japan
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- Ryota Miyata
- Faculty of Life Sciences, Kumamoto University, 5-1 Oe-honmachi Chuo-ku, Kumamoto 862-0973, Japan
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- Hirofumi Matsunaga
- Faculty of Life Sciences, Kumamoto University, 5-1 Oe-honmachi Chuo-ku, Kumamoto 862-0973, Japan
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- Tadao Ishizuka
- Faculty of Life Sciences, Kumamoto University, 5-1 Oe-honmachi Chuo-ku, Kumamoto 862-0973, Japan
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説明
In addition to phosphanes, olefins, amines, and amides, over the past two decades N-heterocyclic carbene (NHC) has emerged as a useful alternative ligand. Based on a number of derivatization studies on NHC ligands, imidazol-2-ylidene and imidazolin-2-ylidene became the standard heterocyclic form, and bulky substituents have commonly been introduced on the nitrogen(s) adjacent to carbenic carbons. Our group previously developed NHCs equipped with noncarbenic carbons with a bicyclic architecture that gives them unique steric properties that make them bulky but accessible. In this study, we synthesized a novel type of NHC ligand that possesses a bicyclo[2.2.1]heptane architecture, and we compared five derivatives using copper-catalyzed allylic arylations with aryl Grignard reagents. The regioselectivity of the substitution obviously indicates that a phenyl ring over an active site has a characteristic effect on the resultant copper catalysts when γ-substitution is the major pathway.
収録刊行物
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 84 (1), 128-139, 2018-12-04
American Chemical Society (ACS)
