Synthesis of Biaryl Compounds through Three-Component Assembly: Ambidentate Effect of the tert-Butyldimethylsilyl Group for Regioselective Diels–Alder and Hiyama Coupling Reactions†
Shuji Akai Prof. Dr.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorTakashi Ikawa Dr.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorSho-ichi Takayanagi
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorYuki Morikawa
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorShinya Mohri
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorMasaya Tsubakiyama
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorMasahiro Egi Dr.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorYasufumi Wada
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871 (Japan)
Search for more papers by this authorYasuyuki Kita Prof. Dr.
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871 (Japan)
Current address: School of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Noji Higashi, Kusatsu, Shiga 525-8577 (Japan)
Search for more papers by this authorShuji Akai Prof. Dr.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorTakashi Ikawa Dr.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorSho-ichi Takayanagi
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorYuki Morikawa
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorShinya Mohri
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorMasaya Tsubakiyama
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorMasahiro Egi Dr.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526 (Japan), Fax: (+81) 54-264-5672
Search for more papers by this authorYasufumi Wada
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871 (Japan)
Search for more papers by this authorYasuyuki Kita Prof. Dr.
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871 (Japan)
Current address: School of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Noji Higashi, Kusatsu, Shiga 525-8577 (Japan)
Search for more papers by this authorThis work was supported by Grants-in-Aid for Scientific Research and the global COE program from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). We thank the Uehara Memorial Foundation for financial support.
Graphical Abstract
Two for the price of one: A method has been developed for the regiocontrolled synthesis of multisubstituted biaryl derivatives. This protocol involves the use of the tert-butyldimethylsilyl (TBDMS) group to direct the regioselective Diels–Alder reaction of a 3-TBDMS-benzyne with a furan derivative and a subsequent Hiyama cross-coupling reaction of the TBDMS group with aryl iodides (see scheme).
Supporting Information
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