Download e-book for kindle: Ionic and Organometallic-Catalyzed Organosilane Reductions by Gerald L. Larson, James L. Fry

By Gerald L. Larson, James L. Fry

ISBN-10: 0470547871

ISBN-13: 9780470547878

An important reference e-book for all man made natural chemistsThe highly helpful chemical-reducing houses of organosilicon hydrides were identified for greater than part a century. because the early discovery of those homes, curiosity within the use of organosilicon hydrides for the aid of natural sensible teams has elevated gradually and has ended in the improvement of many strategies for his or her deployment in chemo-, regio-, and stereoselective variations in natural synthesis.Ionic and Organometallic-Catalyzed Organosilane savings offers an up to date, complete survey of the literature of this wealthy chemistry because it relates to natural synthesis. either ionic and catalyst-mediated response varieties are incorporated, with acceptable connection with response mechanisms the place they've been elucidated. a wide selection of natural useful team discounts via organosilicon hydrides obtain serious reviews and evaluate, in particular with appreciate to scope and barriers. a considerable dialogue of uneven rate reductions can be incorporated during this book.The contents of the booklet are taken from the great overview of the subject inside the natural Reactions sequence and canopy the aid of all natural teams. All recognized examples are compiled in thirty-four simply scanned, finished tables compiled from 809 unique articles. up-to-date lists comprising 256 extra references for the tables are only if carry the assurance as much as March 2009.The authors were, and stay, focused on the functions of organosilanes to natural synthesis. in step with the target of natural Reactions, the content material and presentation of this article emphasize the preparative elements of the rate reductions targeting the scope and boundaries of the person variations besides precise experimental procedures.Ionic and Organometallic-Catalyzed Organosilane savings is a necessary reference ebook for all artificial natural chemists operating in educational and commercial laboratories.

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Extra info for Ionic and Organometallic-Catalyzed Organosilane Reductions (Organic Reactions)

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249 In a like manner, enynes with a vinyl bromide as the olefin function undergo reductive cyclization (Eq. 249 O Cs2CO3, DMF, 80°, 3 h Br EtO2C EtO2C O Et3SiH, Pd(PPh3)4 Br Et3SiH, Pd(PPh3)4 EtO2C Cs2CO3, DMF, 80°, 4 h EtO2C (48%) (Eq. 105) (72%) (Eq.

128 R1 R1 Cl R 2 Et3SiH, CH2Cl2 TFA R2 R2 R1 R2 Me Me t-Bu Me t-Bu t-Bu (79%) (50%) (100%) R2 (Eq. 54) ORGANOSILICON HYDRIDE REDUCTIONS 31 It is clear that the ionizing power of the solvent used is important in many of these reductions. 193 The combination of boron trifluoride etherate and triethylsilane can cause the reduction of tertiary fluoride centers even in polyfunctional compounds (Eq. 194 O Ph O O Ph Et3SiH, BF3•OEt2 O (100%) CH2Cl2, –20°, 8 h F (Eq. 195 The reduction of a β-chloro ether occurs in excellent yield with this system (Eq.

66). Et3SiH O S H+ +S Et3SiH (Eq. 65) (80%) O TFA S (15%) (Eq. 66) 20 h Attempted reduction of vinyl acetate yields a mixture containing 8% ethyl acetate and 3% ethyl trifluoroacetate after 10 hours. 234 Treatment of N -vinyl-3-methyl-6-pyridazone with excess trifluoroacetic acid and triethylsilane at 65◦ for 25 hours yields 67% of the reduced product N -ethyl3-methyl-6-pyridazone (Eq. 235 It is noteworthy that only the vinyl group in this compound undergoes reduction under these conditions, and not the ring or carbonyl sites.

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Ionic and Organometallic-Catalyzed Organosilane Reductions (Organic Reactions) by Gerald L. Larson, James L. Fry

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