By Hisashi Yamamoto, Kazuaki Ishihara
This two-volume set covers all new advancements and, additionally, comprises the recent proposal of mixed Bronsted and Lewis acid catalysis, constructed through Hisashi Yamamoto himself. the wonderful editorial group has prepare an both most sensible workforce of specialist authors, leading to a real treasure trove of crucial info -- making this a needs to for each chemist operating in natural chemistry and catalysis, in academia in addition to in undefined.
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Additional info for Acid Catalysis in Modern Organic Synthesis, vol 1
2007) journal of the American Chemical Society, 1 28, 1 1 90- 5 . 35 Hasegawa, A , Naganawa, Y . , Fushimi, M . , Yamamoto, H . (2006) Organic Letters, 8, 3 1 75 -8. , March, J - (2001) March's Advanced Organic Chemistry, 5th edn, J ohn Wiley & Sons, Inc. , Hasegawa, A, Yamamoto, H . (2001) Angewandte Chemie International Edition, 40, 4077. , Yamamoto, H. (2002) Synlett, 1 296. , Yamamoto, H. (2002) Synlett, 1 299. , Yamamoto, H. (2003) Ange wandte Chemie International Edition, 42, 5 7 3 1 . , H asegawa, A , Kuwata, S .
27 -0. 1 Introd uction of Eiectron-Withdrawing G roup There are many factors which influence acidity. g. g. O H , N H , C H , etc . ) . Therefore, a simple strategy to develop more acidic Br0nsted acid would be to synthesize molecules which bear, along with the acidic site, several electron withdrawing groups andfor n-electron acceptors that form extensive conjugated systems with the anionic center of A- . According to Yagpolskii's principle, Koppel et al. reported that introduction of very strong electron-acceptor substituents such as =NTf and =N S 02 F into an acid 2 system instead of double bonded sp oxygen or sulfur atom increased the stability of counter anions and their acidity [4) .
2 equiv) tol u ene or MeCN. t.. 5 mg) in place of (2) is indicated in brackets. ; I Fig. 3 Fl uoro u s cata lysts recyc l i n g based u pon l i q u idjsolid phase separati o n . sodium 1 H, 1 H-perfluorodecanoxide. This fluorous super Bmnsted acid can be re cycled by using liquidjsolid phase separation without fluorous solvents ( Figure 2 . 3 , Scheme 2 . 5 ) . Various arylbis (triflyl)methanes and various 1 , 1 -bis (triflyl) alkanes have been synthesized from commercially available benzylic halides and 1 -alkanols.