AK-1984GU_published_mainmanuscript

AK-1984GU_published_mainmanuscript - Issue in Honor of...

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Issue in Honor of Prof. Alain Krief ARKIVOC 2007 (x) 10-20 Recent Advances in Bismuth Mediated Aldol and Mannich Reactions Thierry Ollevier,* Valerie Desyroy, and Etienne Nadeau Département de chimie, Université Laval, Québec (Québec) G1K 7P4, Canada E-mail: [email protected] Dedicated to Professor Alain Krief on the occasion of his 65 th birthday Abstract Bismuth metal and bismuth salts have been used for various aldol and Mannich type reactions. Bismuth(III) salts, and bismuth(III) triflate in particular, are cheap and environmentally benign Lewis acids. This account highlights the scope and applications of bismuth(0) and bismuth(III) salts in fundamental reactions like the aldol and Mannich reactions. Various bismuth mediated Mukaiyama aldol and Mannich type reactions are presented. Bismuth(0) mediated Reformatsky and imino Reformatsky reactions are also disclosed in this account. Keywords: Bismuth, Bismuth triflate, Aldol, Mukaiyama aldol, Mannich, Multicomponent reactions, Green chemistry Contents 1. Introduction 2. Bismuth mediated aldol reactions 2.1 Bismuth(III) catalyzed Mukaiyama aldol reactions 2.2 Bismuth(0) mediated Reformatsky reactions 3. Bismuth mediated Mannich type reactions 3.1 Bismuth(III) catalyzed Mannich type reactions 3.1.1 One pot bismuth(III) catalyzed Mannich type reactions 3.1.2 Bismuth(III) catalyzed Mannich type reactions with nitriles 3.2 Bismuth(III) catalyzed Mannich type reactions of N -alkoxycarbonylamino sulfones 3.3 Bismuth(III) catalyzed aziridination reactions 3.4 Bismuth(III) mediated homo Mannich type reactions 3.5 Bismuth(0) mediated imino Reformatsky reactions 4. Conclusions 5. References ISSN 1424-6376 Page 10 © ARKAT-USA, Inc.
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Issue in Honor of Prof. Alain Krief ARKIVOC 2007 (x) 10-20 1. Introduction Bismuth compounds have recently attracted much attention due to low toxicity, low cost, and good stability. 1 Bismuth has an electron configuration of [Xe]4 f 14 5 d 10 6 s 2 6 p 3 , and due to weak shielding of the 4 f electrons, bismuth compounds exhibit Lewis acidity. Among all, bismuth(III) salts have been widely used and were reported as effective catalysts for an array of synthetic transformations: opening of epoxides, 2 formation and deprotection of acetals, 3 Friedel-Crafts reactions, 4 Fries and Claisen rearrangements, 5 and Sakurai reactions. 6 Bismuth triflate [Bi(OTf) 3 ] is particularly attractive due to its commercial availability or ease of preparation from commercially available starting materials. 7 2. Bismuth mediated aldol reactions There has been a few preparations of interest reported for the synthesis of Bi(OTf) 3 . 7 Noteworthy is the work of Torisawa for an expedient preparative protocol and characterization of Bi(OTf) 3 . 8 NMR analysis of Bi(OTf) 3 in acetone- d 6 1 revealed that Bi(OTf) 3 was able to promote the aldol reaction of acetone to yield the corresponding aldol 2 , itself undergoing slow dehydration to mesityl- d oxide 3 . The catalytic activities of a series of prepared metal triflates, including Bi(OTf) 3 , were tested in this aldol reaction on an analytical scale (Scheme 1).
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This note was uploaded on 02/17/2011 for the course CHEMISTRY 101 taught by Professor Csr during the Spring '11 term at University of Louisville.

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AK-1984GU_published_mainmanuscript - Issue in Honor of...

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