ca01 only detailed ToC 1..24
ca01 only detailed ToC 1..24 ca01 only detailed ToC 1..24
28 Biographical Sketch John Montgomery was born in 1965 in Concord, N.C. He received his A.B degree from the University of North Carolina at Chapel Hill in 1987, and he carried out undergraduate research under the direction of Professors Joe Templeton and Maurice Brookhart. He received his Ph.D. at Colorado State University in 1991 under the direction of Professor Lou Hegedus. He was an American Cancer Society Postdoctoral Fellow at the University of California at Irvine from 1991 –1993 with Professor Larry Overman. In 1993, he began his independent career at Wayne State University where he is now Professor of Chemistry. His work at Wayne State has focused on applications of organonickel chemistry in reaction discovery, synthetic methodology development, and total synthesis, and on the development of new methods for the synthesis of amino acids utilizing nitroacetates as glycine templates. He has received a number of awards including an Arthur C. Cope Scholar Award, a Camille Dreyfus Teacher Scholar Award, and an NSF Career Award.
1.1 Product Class 1: Organometallic Complexes of Nickel J. Montgomery 1.1 Product Class 1: Organometallic Complexes of Nickel ..................... 31 1.1.1 Product Subclass 1: Nickel Complexes of 1,3-Dienes ...................... 32 Synthesis of Product Subclass 1 ............................................ 32 1.1.1.1 Method 1: Ligand Exchange with Bis(ç 4 -cycloocta-1,5-diene)nickel(0) ... 32 Applications of Product Subclass 1 in Organic Synthesis ..................... 33 1.1.1.2 Method 2: Diene–Diene Cycloadditions ................................ 33 1.1.1.3 Method 3: Diene–Alkyne Cycloadditions ............................... 34 1.1.1.4 Method 4: Diene–Aldehyde Reductive Cyclizations ..................... 35 1.1.1.4.1 Variation 1: Triethylsilane-Mediated Reactions ........................... 35 1.1.1.4.2 Variation 2: Triethylborane-Mediated Reactions ......................... 36 1.1.1.5 Method 5: 1,4-Dialkylation of Dienes .................................. 36 1.1.1.6 Method 6: Hydrocyanation of Dienes .................................. 37 1.1.2 Product Subclass 2: Nickel–Allyl Complexes ............................... 37 Synthesis of Product Subclass 2 ............................................ 37 1.1.2.1 Method 1: Oxidative Addition of Nickel(0) with Allylic Electrophiles ...... 37 1.1.2.2 Method 2: Addition of Allylmagnesium Halides to Nickel(II) Salts ........ 38 1.1.2.3 Method 3: Oxidative Addition of Nickel(0) with Enones in the Presence of Lewis Acids ................................. 39 1.1.2.4 Method 4: Oxidative Cyclization of Nickel(0) Complexes of Conjugated Dienes ......................................... 40 Applications of Product Subclass 2 in Organic Synthesis ..................... 41 1.1.2.5 Method 5: Coupling of Allyl Halide Derived Nickel–Allyl Complexes with Alkyl Halides and Other Electrophiles ................... 41 1.1.2.6 Method 6: Coupling of Enal-Derived Nickel–Allyl Complexes with Alkyl Halides and Other Electrophiles ................... 42 1.1.2.7 Method 7: Coupling of Nickel–Allyl Complexes with Main Group Organometallics ............................... 44 1.1.2.7.1 Variation 1: Allylic Ether Derived ð-Allyl Complexes ...................... 44 1.1.2.7.2 Variation 2: Enal-Derived ð-Allyl Complexes ............................. 46 1.1.2.7.3 Variation 3: Allylic Alcohol Derived ð-Allyl Complexes .................... 46 1.1.2.8 Method 8: Addition of Stabilized Nucleophiles to Nickel–Allyl Complexes 47 1.1.2.9 Method 9: Alkyne Insertions with Nickel–Allyl Complexes ............... 47 1.1.2.10 Method 10: Alkene Insertions with Nickel–Allyl Complexes ............... 49 1.1.3 Product Subclass 3: Nickel–Alkyne Complexes ............................ 49 Synthesis of Product Subclass 3 ............................................ 50 1.1.3.1 Method 1: Ligand Exchange with Nickel–Alkene Complexes ............. 50 Applications of Product Subclass 3 in Organic Synthesis ..................... 51 1.1.3.2 Method 2: Coupling of Alkynes with Carbon Dioxide .................... 51 1.1.3.3 Method 3: Coupling of Alkynes with Isocyanides ....................... 52 29
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1.1 Product Class 1: Organometallic Complexes of Nickel<br />
J. Montgomery<br />
1.1 Product Class 1: Organometallic Complexes of Nickel ..................... 31<br />
1.1.1 Product Subclass 1: Nickel Complexes of 1,3-Dienes ...................... 32<br />
Synthesis of Product Subclass 1 ............................................ 32<br />
1.1.1.1 Method 1: Ligand Exchange with Bis(ç 4 -cycloocta-1,5-diene)nickel(0) ... 32<br />
Applications of Product Subclass 1 in Organic Synthesis ..................... 33<br />
1.1.1.2 Method 2: Diene–Diene Cycloadditions ................................ 33<br />
1.1.1.3 Method 3: Diene–Alkyne Cycloadditions ............................... 34<br />
1.1.1.4 Method 4: Diene–Aldehyde Reductive Cyclizations ..................... 35<br />
1.1.1.4.1 Variation 1: Triethylsilane-Mediated Reactions ........................... 35<br />
1.1.1.4.2 Variation 2: Triethylborane-Mediated Reactions ......................... 36<br />
1.1.1.5 Method 5: 1,4-Dialkylation of Dienes .................................. 36<br />
1.1.1.6 Method 6: Hydrocyanation of Dienes .................................. 37<br />
1.1.2 Product Subclass 2: Nickel–Allyl Complexes ............................... 37<br />
Synthesis of Product Subclass 2 ............................................ 37<br />
1.1.2.1 Method 1: Oxidative Addition of Nickel(0) with Allylic Electrophiles ...... 37<br />
1.1.2.2 Method 2: Addition of Allylmagnesium Halides to Nickel(II) Salts ........ 38<br />
1.1.2.3 Method 3: Oxidative Addition of Nickel(0) with Enones in<br />
the Presence of Lewis Acids ................................. 39<br />
1.1.2.4 Method 4: Oxidative Cyclization of Nickel(0) Complexes of<br />
Conjugated Dienes ......................................... 40<br />
Applications of Product Subclass 2 in Organic Synthesis ..................... 41<br />
1.1.2.5 Method 5: Coupling of Allyl Halide Derived Nickel–Allyl Complexes<br />
with Alkyl Halides and Other Electrophiles ................... 41<br />
1.1.2.6 Method 6: Coupling of Enal-Derived Nickel–Allyl Complexes<br />
with Alkyl Halides and Other Electrophiles ................... 42<br />
1.1.2.7 Method 7: Coupling of Nickel–Allyl Complexes with<br />
Main Group Organometallics ............................... 44<br />
1.1.2.7.1 Variation 1: Allylic Ether Derived ð-Allyl Complexes ...................... 44<br />
1.1.2.7.2 Variation 2: Enal-Derived ð-Allyl Complexes ............................. 46<br />
1.1.2.7.3 Variation 3: Allylic Alcohol Derived ð-Allyl Complexes .................... 46<br />
1.1.2.8 Method 8: Addition of Stabilized Nucleophiles to Nickel–Allyl Complexes 47<br />
1.1.2.9 Method 9: Alkyne Insertions with Nickel–Allyl Complexes ............... 47<br />
1.1.2.10 Method 10: Alkene Insertions with Nickel–Allyl Complexes ............... 49<br />
1.1.3 Product Subclass 3: Nickel–Alkyne Complexes ............................ 49<br />
Synthesis of Product Subclass 3 ............................................ 50<br />
1.1.3.1 Method 1: Ligand Exchange with Nickel–Alkene Complexes ............. 50<br />
Applications of Product Subclass 3 in Organic Synthesis ..................... 51<br />
1.1.3.2 Method 2: Coupling of Alkynes with Carbon Dioxide .................... 51<br />
1.1.3.3 Method 3: Coupling of Alkynes with Isocyanides ....................... 52<br />
29
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