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30 1.1.3.4 Method 4: Coupling of Alkynes with Aldehydes ......................... 52 1.1.3.5 Method 5: Coupling of Two Alkynes ................................... 55 1.1.3.6 Method 6: Coupling of Alkynes with Alkenes ........................... 56 1.1.3.7 Method 7: [2 +2+2] Cycloadditions .................................... 58 1.1.3.8 Method 8: Alkyne Carbonylation ...................................... 60 1.1.3.9 Method 9: Alkyne Hydrocyanation ..................................... 60 1.1.3.10 Method 10: Alkyne Hydrosilylation ...................................... 60 1.1.3.11 Method 11: Alkyne Carbozincation ..................................... 61 1.1.4 Product Subclass 4: Nickel–Alkene Complexes ............................ 62 Synthesis of Product Subclass 4 ............................................ 62 1.1.4.1 Method 1: Ligand Exchange with Nickel(0) Complexes .................. 62 Applications of Product Subclass 4 in Organic Synthesis 63 1.1.4.2 Method 2: Conjugate Addition to Electrophilic Double Bonds ........... 63 1.1.4.2.1 Variation 1: Organoaluminums ......................................... 63 1.1.4.2.2 Variation 2: Organozincs ............................................... 64 1.1.4.2.3 Variation 3: Organozirconiums ......................................... 66 1.1.4.2.4 Variation 4: Direct Conjugate Addition of Alkyl Halides ................... 67 1.1.4.3 Method 3: Coupling of Two Alkenes ................................... 68 1.1.4.4 Method 4: Alkene Carbonylation ...................................... 71 1.1.4.5 Method 5: Alkene Hydrocyanation ..................................... 72 1.1.4.6 Method 6: Alkene Hydrosilylation ..................................... 73 1.1.4.7 Method 7: Alkene Hydroalumination .................................. 73 1.1.4.8 Method 8: Alkene Hydrozincation ..................................... 75 1.1.4.9 Method 9: Alkene Carbozincation ..................................... 76 1.1.4.10 Method 10: Homo-Diels–Alder Cycloadditions ........................... 77 1.1.4.11 Method 11: Alkene Polymerization ...................................... 77
1.1 Product Class 1: Organometallic Complexes of Nickel J. Montgomery General Introduction This contribution provides an overview of contemporary synthetic methods of broad applicability that involve the preparation and use of nickel ð-complexes as starting materials or reactive intermediates. Numerous excellent reviews on the chemistry of nickel have appeared that are complementary to this contribution in subject and scope. An outstanding review by Chetcuti describes the known ð-complexes of nickel, [1] and several other structural classes of nickel complexes have been reviewed; [2–4] ó-bonded organonickel compounds are reviewed in Houben–Weyl, Vol. 13/9b, pp 632–700. The historical development and early applications of nickel chemistry have been reviewed by Wilke [5] and Jolly, [6] industrial applications have been reviewed by Keim, [7] and several other reviews on specific groups of synthetic transformations have appeared. [8–12,187] The organometallic chemistry of nickel has a rich history dating back more than 100 years. [5] Despite its long history, fundamentally new reactions are still being developed at a rapid pace. Furthermore, existing reactions are being applied in new and creative ways to solve long-standing challenges in organic synthesis. More and more of the synthetic organic community is beginning to realize that nickel catalysis provides preparatively convenient reactions of broad scope in a variety of contexts. In many cases, the reactivity exhibited by nickel may not be achieved by any other transition element. At this time, organonickel chemistry seems to be well poised to provide an increasing number of new reactions and interesting mechanistic questions, as well as to gain an increasingly important role in the organic chemist s repertoire of mainstream synthetic transformations. The most comm<strong>only</strong> employed catalysts in nickel-catalyzed reactions are bis(acetylacetonato)nickel(II) (1), which is commercially available, bis(ç 4 -cycloocta-1,5-diene)nickel(0) (2) which is also commercially available or may be easily prepared (Scheme 1), [13] and dichlorobis(triphenylphosphine)nickel(II) (3) which can also be easily prepared (Scheme 2). [14] SAFETY: Tetracarbonylnickel(0) should be handled with extreme caution due to its volatility and high toxicity. All nickel compounds should be handled with care since many are cancer suspect agents. [188] Scheme 1 Synthesis of Bis(ç 4 -cycloocta-1,5-diene)nickel(0) [13] Ni(acac)2 1 1. cod, THF, −78 oC 2. DIBAL-H, THF, −78 oC 72% Ni(cod)2 2 Scheme 2 Synthesis of Dichlorobis(triphenylphosphine)nickel(II) [14] NiCl 2•6H 2O Ph 3P, AcOH, rt, 24 h 84% NiCl2(PPh3) 2 3 31 for references see p 79
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References 81 [98] Tsuda, T.; Mizun
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86 Biographical Sketches Rinaldo Po
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88 2.6.4.2.2 Variation 2: Two-Elect
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90 2.6 Product Class 6: Organometal
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92 Science of Synthesis 2.6 Complex
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100 Science of Synthesis 2.6 Comple
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141 Science of Synthesis Houben-Wey
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4.4.27 Product Subclass 27: Æ-Halo
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4.4.27 Æ-Haloalkylsilanes 147 Sche
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4.4.27 Æ-Haloalkylsilanes 149 dros
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4.4.27 Æ-Haloalkylsilanes 151 4.4.
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4.4.27 Æ-Haloalkylsilanes 153 In g
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4.4.27 Æ-Haloalkylsilanes 155 4.4.
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4.4.27 Æ-Haloalkylsilanes 157 Æ-H
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References 159 References [1] Haman
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References 161 [93] Bruno, J. W.; S
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164
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166 Biographical Sketches Alan Spiv
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168 5.1.22 Product Subclass 22: Ary
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170 Science of Synthesis 5.1 German
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176 References [43] Eaborn, C.; Var
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178 Abbreviations Chemical (cont.)
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180 Abbreviations Ligands (cont.) 2
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182 Abbreviations General (cont.) q
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