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Synthesis of Vinylstannanes with in Situ Generated Organotin Hydrides

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Synthesis of Vinylstannanes with in Situ Generated Organotin Hydrides SYNTHESIS OF VINYLSTANNANES WITH IN SITU GENERATED ORGANOTIN HYDRIDES By Banibrata Ghosh A DISSERTATION Submitted to Michigan State University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Chemistry 2011 ABSTRACT SYNTHESIS OF VINYLSTANNANES WITH IN SITU GENERATED ORGANOTIN HYDRIDES By Banibrata Ghosh Vinylstannanes are useful intermediates in organic chemistry as they undergo an important C-C bond forming reaction called the Stille coupling. Even though, these species can be accessed by a number of processes, transition-metal-catalyzed hydrostannations of alkynes with organotin hydrides are among the more synthetically attractive methods for their syntheses. Nonetheless, a number of issues, including storage, cost and toxicity associated with organotin hydrides besets the usefulness of hydrostannation protocols. Strategies have been developed to generate organotin hydrides in situ so as to carry out these transformations in more benign ways. Most of these strategies suffer from functional group compatibility issues or require excess tin. Here in, we describe protocols that could be efficiently carried out with in situ generated organotin hydrides under a number of transition-metal catalysts using less toxic organotin fluorides or less expensive organotin chlorides. We have also demonstrated a Lewis-acid mediated one-pot allylation-hydrostannation protocol to access structurally complex vinylstannane products that involves a recycling of the organotin species generated during the allylation step. To my father Bivash Kumar Ghosh and my mother Archana Ghosh iii ACKNOWLEDGMENTS I would like to thank Professor Robert E. Maleczka, Jr., my research adviser for his patience and guidance during my studies at Michiagan State University. I would also like to thank Professor William Wulff, James McCusker, Gary Blanchard and Greg Baker for serving on my guidance committee and Professor William Wulff, Ned Jackson and A. Daniel Jones for their helpful suggestions and advice. My special thanks go to Dr. Daniel Holmes, who very kindly helped me for long hours during the kinetic studies I performed and also with other spectral data related questions. I would also like to take my time to thank my parents. I could not have done it without their sincere love, support and encouragement in every step of the way. I should also thank Harlacher family, Lansing, for their love and support during these years. Finally, I would like to thank my colleagues from the Maleczka group, especially IlHwan and Kim for their friendship and helps and all those friends who never made me realize that I am thousands of miles away from my home. iv TABLE OF CONTENTS LIST OF TABLES ..................................................................................................... vii LIST OF FIGURES .................................................................................................. viii LIST OF SCHEMES ..................................................................................................ix LIST OF ABBREVIATIONS .......................................................................................xi Chapter 1. An Introduction..........................................................................................1 Chapter 2. Non-palladium transition-metal-catalyzed hydrostannation reactions with Bu3SnF / PMHS/ catalytic TBAF as an in situ tin hydride source ..............................6 2.1. Introduction ...................................................................................................6 2.2. Initial work...................................................................................................17 2.3. Results and discussions .............................................................................18 2.3.1. Molybdenum catalyzed hydrostannations .........................................18 2.3.2. Nickel catalyzed hydrostannations ....................................................24 2.3.3. Cobalt catalyzed hydrostannations ...................................................26 2.3.4. Rhodium and ruthenium catalyzed hydrostannations........................27 2.4. Conclusions ...............................................................................................29 Chapter 3. Non-palladium transition-metal-catalyzed hydrostannation reactions with Bu3SnCl / PMHS/ KF / 18-crown-6 as an in situ tin hydride source..........................30 3.1. Introduction ..........................................................................................30 3.2. Initial study ...........................................................................................31 3.3. Nickel catalyzed hydrostannations .......................................................33 3.4. Cobalt catalyzed hydrostannations ......................................................35 3.5. Molybdenum catalyzed hydrostannations ............................................36 3.6. Rhodium and ruthenium catalyzed hydrostannations...........................41 3.7. Conclusions..........................................................................................48 Chapter 4. Development of one-pot allylation-hydrostannation sequence involving recycling of tin...........................................................................................................49 4.1. Introduction .................................................................................................49 4.2. Results and discussions .............................................................................54 4.3. Conclusions ................................................................................................71 v Chapter 5. Mechanistic investigation of Lewis acid catalyzed one-pot allylation- hydrostannation sequence........................................................................................72 5.1. Introduction .................................................................................................72 5.2. Results and disussions ...............................................................................75 5.3. Conclusions ................................................................................................85 Chapter 6. Experimental details................................................................................86 REFERENCES .......................................................................................................142 vi LIST OF TABLES Table 1. MoBI3-catalyzed hydrostannations of terminal alkynes ..............................21 Table 2. MoBI3-catalyzed hydrostannations of alkynyl esters...................................24 Table 3. NiCl2(PPh3)2-catalyzed hydrostannations ..................................................26 Table 4. CoCl2(PPh3)2-catalyzed hydrostannations .................................................27 Table 5. Rhodium and Ruthenium-catalyzed hydrostannations................................28 Table 6. Optimization of one-pot allylation-hydrostannation sequence.....................56 Table 7. Optimization of the work-up ........................................................................60 Table 8. Results of one-pot allylation-hydrostannation protocols..............................66 vii LIST OF FIGURES Figure 1. Reactions of vinylstannanes........................................................................1 Figure 2. Mechanism of radical hydrostannation reactions.........................................9 Figure 3. Sonochemical hydrostannation of terminal alkynes...................................10 Figure 4. Mechanism of transition-metal catalyzed hydrostannations ......................13 Figure 5. Organotin hydrides to solve separation and/or other related issues..........15 Figure 6. Proposed mechanism of MoBI3-catalyzed hydrostannations ....................23 Figure 7. Mechanism of formation of Z-isomer proposed by Oshima .......................25 Figure 8. Synthetic utility of homoallylic alcohols......................................................50 Figure 9. Prospective alkynals for one-pot allylation-hydrostannations ....................61 Figure 10. One-pot allylation-hydrostannation protocols ..........................................65 Figure 11. Lewis acid-catalyzed hydrostannation mechanism of alkynes.................69 Figure 12. 119Sn NMR spectrum of intermediate II...................................................77 119 Figure 13. Sn NMR spectrum of premixed allylstannane and BF3•OEt2 ..............78 Figure 14. Fluorine-decoupled spectrum of Intermediate III .....................................79 Figure 15. 119Sn NMR spectrum of the mixture after addition of PMHS and B(C6F5)3 ...................................................................................................................80 Figure 16. 119Sn NMR spectrum of Intermediate V ..................................................81 viii LIST OF SCHEMES Scheme 1. In situ generated organotin hydrides in hydrostannations ........................3 Scheme 2. One-pot hydrostannation/Stille coupling sequence...................................5 Scheme 3. Synthesis of vinylstannanes using different methods ...............................7 Scheme 4. Et3B induced radical addition of organotin hydrides to alkynes ..............10 Scheme 5. Stoichiometric stannylcupration..............................................................11 Scheme 6. Transition-metal catalyzed stannylmetalation of alkynes........................12 Scheme 7. Fluoride-catalyzed silane reductions
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