Allylation of Imines and Their
Derivatives with Organoboron Reagents: Stereocontrolled
Synthesis of Homoallylic Amines

Timothy R. Ramadhar; Robert A. Batey

doi:10.1055/s-0030-1258434

REVIEW

Allylation of Imines and Their Derivatives with Organoboron Reagents: Stereocontrolled Synthesis of Homoallylic Amines

Timothy R. Ramadhar, Robert A. Batey*
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada
Fax: +1(416)9785059; e-Mail: rbatey@chem.utoronto.ca;

Abstract

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Abstract

Homoallylic amines serve as important precursors for the synthesis of a variety of natural products and pharmaceutically relevant compounds. One widely used strategy for homoallylic amine synthesis is the addition of allylic metal or metalloid derivatives to imines or related functional groups. The use of allylic boron compounds for these reactions has emerged as an important synthetic approach, providing a robust and chemoselective method for efficient and stereocontrolled access to various homoallylic amines. In this review, a comprehensive and critical analysis of imine allylboration and crotylboration methods using organoborane, organoboronate and potassium organotrifluoroborate reagents is provided. These approaches include direct methods that accomplish diastereo- or enantiocontrolled addition of the organoboron species. Additionally, organoboron-based transition-metal-catalyzed allylation of imines and their respective surrogates using copper, indium, iridium, palladium or zinc catalysis is discussed. Finally, coverage on the use of allenyl- and propargylboron compounds and their application for the synthesis of homopropargylic and homoallenyl amines is provided.

1 Introduction

2 Organoborane Reagents

3 Organoboronic Acid and Ester Reagents

4 Potassium Organotrifluoroborate Reagents

5 Organoboron-Based Transition-Metal-Catalyzed Allylation

5.1 Copper Catalysis

5.2 Indium Catalysis

5.3 Iridium Catalysis

5.4 Palladium Catalysis

5.5 Zinc Catalysis

6 Allenylation and Propargylation Reactions

7 Concluding Remarks

Key words

allylation - amines - boron - imines - stereoselective synthesis

Full Text

References

<A NAME="RE28810SS-1">1</A> Lawrence SA. Amines: Synthesis, Properties and Applications Cambridge University Press; Cambridge UK: 2004.

For some earlier reviews based exclusively on the addition of allyl nucleophiles to unsaturated C-N functionalities, see:

<A NAME="RE28810SS-2A">2a</A> Ding H. Friestad GK. Synthesis 2005, 2815

<A NAME="RE28810SS-2B">2b</A> Merino P. Tejero T. Delso JI. Mannucci V. Curr. Org. Synth. 2005, 2: 479

<A NAME="RE28810SS-2C">2c</A> Gung BW. Org. React. 2004, 64: 1

<A NAME="RE28810SS-2D">2d</A> Kobayashi S. Sugiura M. Ogawa C. Adv. Synth. Catal. 2004, 346: 1023

<A NAME="RE28810SS-2E">2e</A> Yamamoto Y. Asao N. Chem. Rev. 1993, 93: 2207

<A NAME="RE28810SS-2F">2f</A> Puentes CO. Kouznetsov V. J. Heterocycl. Chem. 2002, 39: 595

<A NAME="RE28810SS-3A">3a</A> Stereodirected Synthesis with Organoboranes Trost BM. Springer; Berlin: 1995.

<A NAME="RE28810SS-3B">3b</A> Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine Hall DG. Wiley-VCH; Weinheim: 2005.

<A NAME="RE28810SS-4A">4a</A> Kennedy JWJ. Hall DG. Angew. Chem. Int. Ed. 2003, 42: 4732 ; Angew. Chem. 2003, 115, 4880

<A NAME="RE28810SS-4B">4b</A> Gravel M. Lachance H. Lu X. Hall DG. Synthesis 2004, 1290

<A NAME="RE28810SS-4C">4c</A> Hall DG. Synlett 2007, 1644

<A NAME="RE28810SS-4D">4d</A> Lachance H. Hall DG. Org. React. 2007, 73: 1

<A NAME="RE28810SS-4E">4e</A> Elford TG. Hall DG. Synthesis 2010, 893

For some reviews dealing with general nucleophilic additions to imines, including allylation, and a description of associated problems, see:

<A NAME="RE28810SS-5A">5a</A> Risch N. Arend M. In Houben-Weyl: Stereoselective Synthesis Vol. E21b: Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Georg Thieme Verlag; Stuttgart: 1995. p.1894

<A NAME="RE28810SS-5B">5b</A> Arend M. Angew. Chem. Int. Ed. 1999, 38: 2873 ; Angew. Chem. 1999, 111, 3047

<A NAME="RE28810SS-5C">5c</A> Kobayashi S. Ishitani H. Chem. Rev. 1999, 99: 1069

<A NAME="RE28810SS-5D">5d</A> Bloch R. Chem. Rev. 1998, 98: 1407

<A NAME="RE28810SS-5E">5e</A> Enders D. Reinhold U. Tetrahedron: Asymmetry 1997, 8: 1895

<A NAME="RE28810SS-5F">5f</A> Friestad G. K. Mathies A. K. Tetrahedron 2007, 63: 2541

<A NAME="RE28810SS-5G">5g</A> Ferraris D. Tetrahedron 2007, 63: 9581

<A NAME="RE28810SS-6">6</A> For an alternate and brief review on allylations with organoboranes, see: Ramachandran PV. Burghardt TE. Pure Appl. Chem. 2006, 78: 1397

<A NAME="RE28810SS-7A">7a</A> Bubnov YN. Mikhailov BM. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1967, 16: 467 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 472

<A NAME="RE28810SS-7B">7b</A> Bubnov YN. Bogdanov VS. Mikhailov BM. J. Obshch. Khim. 1968, 38: 260

<A NAME="RE28810SS-8">8</A> Meller A. Gerger W. Monatsh. Chem. 1974, 105: 684

<A NAME="RE28810SS-9">9</A> Yamamoto Y. Komatsu T. Maruyama K. J. Am. Chem. Soc. 1984, 106: 5031

<A NAME="RE28810SS-10">10</A> Yamamoto Y. Ito W. Maruyama K. J. Chem. Soc., Chem. Commun. 1984, 1004

<A NAME="RE28810SS-11">11</A> Yamamoto Y. Komatsu T. Maruyama K. J. Org. Chem. 1985, 50: 3115

Boat-like transition state models 17 and 20 are shown in different conformations to the models shown in ref. 11 out of clarity. Enantiomeric transition states are not shown.

<A NAME="RE28810SS-13">13</A> Yamamoto Y. Nishii S. Maruyama K. Komatsu T. Ito W. J. Am. Chem. Soc. 1986, 108: 7778

<A NAME="RE28810SS-14">14</A> Yamamoto Y. Ito W. Maruyama K. J. Chem. Soc., Chem. Commun. 1985, 1131

<A NAME="RE28810SS-15">15</A> Yamamoto Y. Ito W. Tetrahedron 1988, 44: 5415

<A NAME="RE28810SS-16A">16a</A> Bubnov YN. In Current Topics in the Chemistry of Boron Kabalka GW. Royal Society of Chemistry; Cambridge UK: 1994. p.44

<A NAME="RE28810SS-16B">16b</A> Bubnov YN. Pure Appl. Chem. 1994, 66: 235

<A NAME="RE28810SS-16C">16c</A> Bubnov YN. Russ. Chem. Bull. 1995, 44: 1156 ; Izv. Akad. Nauk, Ser. Khim. 1995, 1203

<A NAME="RE28810SS-17A">17a</A> Bubnov YN. Shagova EA. Evchenko SV. Ignatenko AV. Gridnev ID. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1991, 40: 2315 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2644

<A NAME="RE28810SS-17B">17b</A> Bubnov YN. Shagova EA. Evchenko SV. Dekaprilevich MO. Struchkov YT. Russ. Chem. Bull. 1994, 657 ; Izv. Akad. Nauk, Ser. Chim. 1994, 705

<A NAME="RE28810SS-17C">17c</A> Bubnov YN. Shagova EA. Evchenko SV. Ignatenko AV. Russ. Chem. Bull. 1994, 43: 645 ; Izv. Akad. Nauk, Ser. Khim. 1994, 693

<A NAME="RE28810SS-17D">17d</A> Bubnov YN. Klimkina EV. Dekaprilevich MO. Struchkov YT. Russ. Chem. Bull. 1996, 45: 2595 ; Izv. Akad. Nauk, Ser. Khim. 1996, 2736

<A NAME="RE28810SS-17E">17e</A> Bubnov YN. Klimkina EV. Ignatenko AV. Gridnev ID. Tetrahedron Lett. 1996, 37: 1317

<A NAME="RE28810SS-17F">17f</A> Bubnov YN. In Advanced Boron Chemistry Siebert W. Royal Society of Chemistry; Cambridge UK: 1997. p.123

<A NAME="RE28810SS-17G">17g</A> Bubnov YN. Demina EE. Ignatenko AV. Russ. Chem. Bull. 1997, 46: 606 ; Izv. Akad. Nauk, Ser. Khim. 1997, 627

<A NAME="RE28810SS-17H">17h</A> Bubnov YN. Demina EE. Ignatenko AV. Russ. Chem. Bull. 1997, 46: 1306 ; Izv. Akad. Nauk, Ser. Khim. 1997, 1361

<A NAME="RE28810SS-17I">17i</A> Bubnov YN. Demina EE. Dekaprilevich MO. Struchkov YT. Russ. Chem. Bull. 1997, 46: 1356 ; Izv. Akad. Nauk, Ser. Khim. 1997, 1413

<A NAME="RE28810SS-17J">17j</A> Bubnov YN. Klimkina EV. Ignatenko AV. Russ. Chem. Bull. 1998, 47: 451 ; Izv. Akad. Nauk, Ser. Khim. 1998, 467

<A NAME="RE28810SS-17K">17k</A> Bubnov YN. Klimkina EV. Ignatenko AV. Russ. Chem. Bull. 1998, 47: 941 ; Izv. Akad. Nauk, Ser. Khim. 1998, 971

<A NAME="RE28810SS-17L">17l</A> Bubnov YN. Demina EE. Belsky VK. Zatonsky GV. Ignatenko AV. Russ. Chem. Bull. 1998, 47: 2249 ; Izv. Akad. Nauk, Ser. Khim. 1998, 2320

<A NAME="RE28810SS-17M">17m</A> Bubnov YN. Klimkina EV. Starikova ZA. Ignatenko AV. Russ. Chem. Bull. 2001, 50: 1078 ; Izv. Akad. Nauk, Ser. Khim. 2001, 1032

<A NAME="RE28810SS-18A">18a</A> Bubnov YN. Shagova SV. Evchenko SV. Ignatenko AV. Russ. Chem. Bull. 1993, 42: 1610 ; Izv. Akad. Nauk, Ser. Khim. 1993, 1672

<A NAME="RE28810SS-18B">18b</A> Bubnov YN. Klimkina EV. Ignatenko AV. Gridnev ID. Tetrahedron Lett. 1997, 38: 4631

<A NAME="RE28810SS-19A">19a</A> Bubnov YN. Evchenko SV. Ignatenko AV. Russ. Chem. Bull. 1993, 42: 1268 ; Izv. Akad. Nauk, Ser. Khim. 1993, 1325

<A NAME="RE28810SS-19B">19b</A> Bubnov YN. Zykov AY. Ignatenko AV. Mikhailovsky AG. Shklyaev YV. Shklyaev VS. Russ. Chem. Bull. 1996, 890 ; Izv. Akad. Nauk, Ser. Khim. 1996, 935

<A NAME="RE28810SS-19C">19c</A> Bubnov YN. Klimkina EV. Ignatenko AG. Russ. Chem. Bull. 1998, 47: 1175 ; Izv. Akad. Nauk, Ser. Khim. 1998, 1206

<A NAME="RE28810SS-19D">19d</A> Mikhailovskii AG. Bubnov YN. Syropyatov BY. Dolzhenko AV. Timofeeva YP. Pharm. Chem. J. 1999, 33: 128 ; Khim.-Farm. Zh. 1999, 33, 15

<A NAME="RE28810SS-19E">19e</A> Pastukhov FV. Yampolsky IV. Bubnov YN. J. Organomet. Chem. 2002, 657: 123

<A NAME="RE28810SS-20">20</A> Bubnov YN. Evchenko SV. Ignatenko AV. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1992, 41: 2239 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1992, 2815

<A NAME="RE28810SS-21">21</A> Bubnov YN. Gurskii ME. Potapova TV. Russ. Chem. Bull. 1996, 45: 2665 ; Izv. Akad. Nauk, Ser. Khim. 1996, 2807

<A NAME="RE28810SS-22A">22a</A> Bubnov YN. Lavrinovich LI. Zykov AY. Klimkina EV. Ignatenko AV. Russ. Chem. Bull. 1993, 1269 ; Izv. Akad. Nauk, Ser. Khim. 1993, 1327

<A NAME="RE28810SS-22B">22b</A> Bubnov YN. Zhun IV. Klimkina EV. Ignatenko AV. Starikova ZA. Eur. J. Org. Chem. 2000, 3323

<A NAME="RE28810SS-23">23</A> Bubnov YN. Klimkina EV. Lavrinovich LI. Zykov AY. Ignatenko AV. Russ. Chem. Bull. 1999, 48: 1696 ; Izv. Akad. Nauk, Ser. Khim. 1999, 1718

<A NAME="RE28810SS-24">24</A> Gurskii ME. Potapova TV. Bubnov YN. Russ. Chem. Bull. 1998, 47: 1410 ; Izv. Akad. Nauk, Ser. Khim. 1998, 1450

<A NAME="RE28810SS-25">25</A> Bubnov Y. N., Zykov A. Y., Lavrinovich L. I., Ignatenko A. V.; Russ. Chem. Bull.; 1993, 42: 1271; Izv. Akad. Nauk, Ser. Khim. 1993, 1329

<A NAME="RE28810SS-26">26</A> Bubnov YN. Zheludeva VI. Rudashevskaya TY. Kuznetsova TS. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1989, 38: 1073 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1179

<A NAME="RE28810SS-27">27</A> Lavrinovich LI. Ignatenko AV. Bubnov YN. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1992, 41: 2051 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1992, 2597

<A NAME="RE28810SS-28">28</A> Bubnov YN. Pastukhov FV. Yampolsky IV. Ignatenko AV. Eur. J. Org. Chem. 2000, 1503

<A NAME="RE28810SS-29A">29a</A> Bespalova NB. Shuvalova OV. Zaikin VG. Borisov RS. Pastukhov FV. Bubnov YN. Russ. Chem. Bull. 2002, 51: 645 ; Izv. Akad. Nauk, Ser. Khim. 2002, 596

<A NAME="RE28810SS-29B">29b</A> Nieczypor P. Mol JC. Bespalova NB. Bubnov YN. Eur. J. Org. Chem. 2004, 812

<A NAME="RE28810SS-29C">29c</A> Kuznetsov NY. Zhun IV. Khrustalev VN. Bubnov YN. Russ. Chem. Bull. 2005, 2229 ; Izv. Akad. Nauk, Ser. Khim. 2005, 2160

<A NAME="RE28810SS-29D">29d</A> Bubnov YN. Kuznetsov NY. Gurskii ME. Semenova AK. Kolomnikova GD. Potapova TV. Pure Appl. Chem. 2006, 78: 1357

<A NAME="RE28810SS-29E">29e</A> Kuznetsov NY. Khrustalev VN. Godovikov IA. Bubnov YN. Eur. J. Org. Chem. 2006, 113

<A NAME="RE28810SS-29F">29f</A> Kuznetsov NY. Lyssenko KA. Peregudov AS. Bubnov YN. Russ. Chem. Bull. 2007, 56: 1569 ; Izv. Akad. Nauk, Ser. Khim. 2007, 1510

<A NAME="RE28810SS-29G">29g</A> Kuznetsov NY. Kolomnikova GD. Khrustalev VN. Golovanov DG. Bubnov YN. Eur. J. Org. Chem. 2008, 5647

<A NAME="RE28810SS-29H">29h</A> Bubnov YN. Gurskii ME. Erdyakov SY. Kizas OA. Kolomnikova GD. Kuznetsov NY. Potapova TV. Varzatskii OA. Voloshin YZ. J. Organomet. Chem. 2009, 694: 1754

<A NAME="RE28810SS-30">30</A> Isono N. Mori M. J. Org. Chem. 1995, 60: 115

<A NAME="RE28810SS-31">31</A> For a review, see: Bubnov YN. Klimkina EV. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35: 888 ; and references therein

<A NAME="RE28810SS-32">32</A> Schkeryantz JM. Woo JCG. Danishefsky SJ. J. Am. Chem. Soc. 1995, 117: 7025

<A NAME="RE28810SS-33">33</A> Depew KM. Danishefsky SJ. Rosen N. Sepp-Lorenzino L. J. Am. Chem. Soc. 1996, 118: 12463

<A NAME="RE28810SS-34A">34a</A> Brown HC. Jadhav PK. J. Am. Chem. Soc. 1983, 105: 2092

<A NAME="RE28810SS-34B">34b</A> Brown HC. Bhat KS. J. Am. Chem. Soc. 1986, 108: 293

<A NAME="RE28810SS-34C">34c</A> Brown HC. Jadhav PK. Bhat KS. J. Am. Chem. Soc. 1988, 110: 1535

<A NAME="RE28810SS-34D">34d</A> Ramachandran PV. Aldrichimica Acta 2002, 35: 23

<A NAME="RE28810SS-35">35</A> Watanabe K. Ito K. Itsuno S. Tetrahedron: Asymmetry 1995, 6: 1531

<A NAME="RE28810SS-36">36</A> Chen G.-M. Ramachandran PV. Brown HC. Angew. Chem. Int. Ed. 1999, 38: 825 ; Angew. Chem. 1999, 111, 828

<A NAME="RE28810SS-37">37</A> Brown HC. Racherla US. Pellechia PJ. J. Org. Chem. 1990, 55: 1868

<A NAME="RE28810SS-38">38</A> Ramachandran PV. Burghardt TE. Chem. Eur. J. 2005, 11: 4387

<A NAME="RE28810SS-39">39</A> Watanabe K. Kuroda S. Yokoi A. Ito K. Itsuno S. J. Organomet. Chem. 1999, 581: 103

<A NAME="RE28810SS-40">40</A> Ramachandran PV. Burghardt TE. Bland-Berry L. J. Org. Chem. 2005, 70: 7911

<A NAME="RE28810SS-41">41</A> Ramachandran PV. Biswas D. Org. Lett. 2007, 9: 3025

<A NAME="RE28810SS-42">42</A> Ramachandran PV. Reddy GV. Biswas D. J. Fluorine Chem. 2009, 130: 204

<A NAME="RE28810SS-43">43</A> Ramachandran PV. Biswas D. Krzeminski MP. Chen G.-M. Tetrahedron Lett. 2010, 51: 332

<A NAME="RE28810SS-44">44</A> Hernandez E. Canales E. Gonzalez E. Soderquist JA. Pure Appl. Chem. 2006, 78: 1389

<A NAME="RE28810SS-45A">45a</A> Burgos CH. Canales E. Matos K. Soderquist JA. J. Am. Chem. Soc. 2005, 127: 8044

<A NAME="RE28810SS-45B">45b</A> Román JG. Soderquist JA. J. Org. Chem. 2007, 72: 9772

<A NAME="RE28810SS-45C">45c</A> Soto-Cairoli B. Soderquist JA. Org. Lett. 2009, 11: 401

<A NAME="RE28810SS-46">46</A> Canales E. Prasad KG. Soderquist JA. J. Am. Chem. Soc. 2005, 127: 11572

<A NAME="RE28810SS-47">47</A> Canales E. Hernandez E. Soderquist JA. J. Am. Chem. Soc. 2006, 128: 8712

<A NAME="RE28810SS-48">48</A> González AZ. Román JG. Alicea E. Canales E. Soderquist JA. J. Am. Chem. Soc. 2009, 131: 1269

<A NAME="RE28810SS-49">49</A> Muñoz-Hernández L. Soderquist JA. Org. Lett. 2009, 11: 2571

<A NAME="RE28810SS-50">50</A> Hoffmann RW. Eichler G. Endesfelder A. Liebigs Ann. Chem. 1983, 2000

<A NAME="RE28810SS-51">51</A> Hoffmann RW. Endesfelder A. Liebigs Ann. Chem. 1986, 1823

<A NAME="RE28810SS-52">52</A> Hoffmann RW. Endesfelder A. Liebigs Ann. Chem. 1987, 215

<A NAME="RE28810SS-53">53</A> Wuts PGM. Jung Y.-W. Tetrahedron Lett. 1986, 27: 2079

<A NAME="RE28810SS-54">54</A> Wuts PGM. Jung Y.-W. J. Org. Chem. 1991, 56: 365

For reviews on the Peterson olefination, see:

<A NAME="RE28810SS-55A">55a</A> Ager DJ. Org. React. 1990, 38: 1

<A NAME="RE28810SS-55B">55b</A> van Staden LF. Gravestock D. Ager DJ. Chem. Soc. Rev. 2002, 31: 195

<A NAME="RE28810SS-56A">56a</A> Roush WR. Hoong LK. Palmer MAJ. Park JC. J. Org. Chem. 1990, 55: 4109

<A NAME="RE28810SS-56B">56b</A> Roush WR. Hoong LK. Palmer MAJ. Straub JA. Palkowitz AD. J. Org. Chem. 1990, 55: 4117

<A NAME="RE28810SS-57">57</A> Itsuno S. Watanabe K. Ito K. El-Shehawy AA. Sarhan AA. Angew. Chem. Int. Ed. 1997, 36: 109 ; Angew. Chem. 1997, 109, 105

<A NAME="RE28810SS-58">58</A> Itsuno S. Watanabe K. Matsumoto T. Kuroda S. Yokoi A. El-Shehawy A. J. Chem. Soc., Perkin Trans. 1 1999, 2011

<A NAME="RE28810SS-59">59</A> Itsuno S. Watanabe K. El-Shehawy AA. Adv. Synth. Catal. 2001, 343: 89

<A NAME="RE28810SS-60">60</A> Chataigner I. Zammattio F. Lebreton J. Villiéras J. Synlett 1998, 275

<A NAME="RE28810SS-61">61</A> Nyzam V. Belaud C. Villiéras J. Tetrahedron Lett. 1993, 34: 6899

<A NAME="RE28810SS-62">62</A> Chataigner I. Zammattio F. Lebreton J. Villiéras J. Tetrahedron 2008, 64: 2441

<A NAME="RE28810SS-63">63</A> Sugiura M. Hirano K. Kobayashi S. J. Am. Chem. Soc. 2004, 126: 7182

<A NAME="RE28810SS-64">64</A> Kobayashi S. Hirano K. Sugiura M. Chem. Commun. 2005, 104

<A NAME="RE28810SS-65">65</A> Sugiura M. Mori C. Hirano K. Kobayashi S. Can. J. Chem. 2005, 83: 937

<A NAME="RE28810SS-66">66</A> Elford TG. Hall DG. Tetrahedron Lett. 2008, 49: 6995

<A NAME="RE28810SS-67">67</A> Elford TG. Ulaczyk-Lesanko A. De Pascale G. Wright GD. Hall DG. J. Comb. Chem. 2009, 11: 155

<A NAME="RE28810SS-68">68</A> Dhudshia B. Tiburcio J. Thadani AN. Chem. Commun. 2005, 5551

<A NAME="RE28810SS-69">69</A> Sieber JD. Morken JP. J. Am. Chem. Soc. 2006, 128: 74

<A NAME="RE28810SS-70">70</A> Pelz NF. Woodward AR. Burks HE. Sieber JD. Morken JP. J. Am. Chem. Soc. 2004, 126: 16328

<A NAME="RE28810SS-71">71</A> Wu TR. Chong JM. J. Am. Chem. Soc. 2006, 128: 9646

<A NAME="RE28810SS-72">72</A> Lou S. Moquist PN. Schaus SE. J. Am. Chem. Soc. 2007, 129: 15398

<A NAME="RE28810SS-73">73</A> Lou S. Moquist PN. Schaus SE. J. Am. Chem. Soc. 2006, 128: 12660

<A NAME="RE28810SS-74">74</A> Paton RS. Goodman JM. Pellegrinet SC. Org. Lett. 2009, 11: 37

<A NAME="RE28810SS-75A">75a</A> Selander N. Kipke A. Sebelius S. Szabó KJ. J. Am. Chem. Soc. 2007, 129: 13723

<A NAME="RE28810SS-75B">75b</A> Selander N. Szabó KJ. Dalton Trans. 2009, 6267

For reviews of organotrifluoroborates and other leading references, see:

<A NAME="RE28810SS-76A">76a</A> Molander GA. Ellis N. Acc. Chem. Res. 2007, 40: 275

<A NAME="RE28810SS-76B">76b</A> Stefani HA. Cella R. Vieira AS. Tetrahedron 2007, 63: 3623

<A NAME="RE28810SS-76C">76c</A> Darses S. Genêt J.-P. Chem. Rev. 2008, 108: 288

<A NAME="RE28810SS-77A">77a</A> Batey RA. Thadani AN. Smil DV. Tetrahedron Lett. 1999, 40: 4289

<A NAME="RE28810SS-77B">77b</A> Batey RA. Thadani AN. Smil DV. Lough AJ. Synthesis 2000, 990

<A NAME="RE28810SS-77C">77c</A> Thadani AN. Batey RA. Org. Lett. 2002, 4: 3827

<A NAME="RE28810SS-77D">77d</A> Thadani AN. Batey RA. Tetrahedron Lett. 2003, 44: 8051

<A NAME="RE28810SS-77E">77e</A> Nowrouzi F. Thadani AN. Batey RA. Org. Lett. 2009, 11: 2631

<A NAME="RE28810SS-77F">77f</A> Nowrouzi F. Janetzko J. Batey RA. Org. Lett. 2010, 12: 5490

<A NAME="RE28810SS-78">78</A> Li S.-W. Batey RA. Chem. Commun. 2004, 1382

For reviews, see:

<A NAME="RE28810SS-79A">79a</A> Batey RA. In Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine Hall DG. Wiley-VCH; Weinheim: 2005. p.279

<A NAME="RE28810SS-79B">79b</A> Petasis NA. In Multicomponent Reactions Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. p.199

<A NAME="RE28810SS-79C">79c</A> Candeias NR. Montalbano F. Cal PMSD. Gois PMP. Chem. Rev. 2010, 110: 6169

<A NAME="RE28810SS-80">80</A> Tremblay-Morin J.-P. Raeppel S. Gaudette F. Tetrahedron Lett. 2004, 45: 3471

<A NAME="RE28810SS-81">81</A> For an alternative review, see: Yoo W.-J. Li C.-J. ChemSusChem 2009, 2: 205

<A NAME="RE28810SS-82">82</A> Wada R. Shibuguchi T. Makino S. Oisaki K. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2006, 128: 7687

<A NAME="RE28810SS-83">83</A> Nicolaou KC. Mathison CJN. Montagnon T. J. Am. Chem. Soc. 2004, 126: 5192

<A NAME="RE28810SS-84">84</A> Kanai M. Wada R. Shibuguchi T. Shibasaki M. Pure Appl. Chem. 2008, 80: 1055

<A NAME="RE28810SS-85">85</A> Schneider U. Chen I. Kobayashi S. Org. Lett. 2008, 10: 737

<A NAME="RE28810SS-86">86</A> Kobayashi S. Konishi H. Schneider U. Chem. Commun. 2008, 2313

<A NAME="RE28810SS-87">87</A> Chakrabarti A. Konishi H. Yamaguchi M. Schneider U. Kobayashi S. Angew. Chem. Int. Ed. 2010, 49: 1838 ; Angew. Chem. 2010, 122, 1882

<A NAME="RE28810SS-88">88</A> Barker TJ. Jarvo ER. Org. Lett. 2009, 11: 1047

<A NAME="RE28810SS-89">89</A> Sebelius S. Wallner OA. Szabó KJ. Org. Lett. 2003, 5: 3065

<A NAME="RE28810SS-90">90</A> Sebelius S. Szabó KJ. Eur. J. Org. Chem. 2005, 2539

<A NAME="RE28810SS-91">91</A> Solin N. Wallner OA. Szabó KJ. Org. Lett. 2005, 7: 689

<A NAME="RE28810SS-92">92</A> For a review of the work in the Szabó group involving palladium-pincer complexes, see: Szabó KJ. Synlett 2006, 811

<A NAME="RE28810SS-93">93</A> Wallner OA. Szabó KJ. Chem. Eur. J. 2006, 12: 6976

<A NAME="RE28810SS-94">94</A> Aydin J. Jumar JS. Sayah MJ. Wallner OA. Szabó KJ. J. Org. Chem. 2007, 72: 4689

<A NAME="RE28810SS-95">95</A> Fujita M. Nagano T. Schneider U. Hamada T. Ogawa C. Kobayashi S. J. Am. Chem. Soc. 2008, 130: 2914

For some examples, see:

<A NAME="RE28810SS-96A">96a</A> Song Y. Oakamoto S. Sato F. Tetrahedron Lett. 2002, 43: 8635

<A NAME="RE28810SS-96B">96b</A> Kumareswaran R. Gallucci J. RajanBabu TV. J. Org. Chem. 2004, 69: 9151

<A NAME="RE28810SS-96C">96c</A> Kaden S. Brockmann M. Reissig H.-U. Helv. Chim. Acta 2005, 88: 1826

<A NAME="RE28810SS-96D">96d</A> Ferreira F. Botuha C. Chemla F. Peréz-Luna A. J. Org. Chem. 2009, 74: 2238

<A NAME="RE28810SS-97A">97a</A> Moreau JL. In The Chemistry of Ketenes, Allenes, and Related Compounds, Part 1 Patai S. John Wiley & Sons; New York: 1980. p.363

<A NAME="RE28810SS-97B">97b</A> Yamamoto H. In Comprehensive Organic Synthesis: Addition to C-X π Bonds Part II Trost BM. Fleming I. Pergamon Press; Oxford: 1991. p.81

<A NAME="RE28810SS-97C">97c</A> Epsztein R. In Comprehensive Carbanion Chemistry Buncel E. Durst T. Wiley; New York: 1980. p.107

<A NAME="RE28810SS-97D">97d</A> Brandsma L. Verkruijsee HD. Synthesis of Acetylenes, Allenes and Cumelenes Elsevier; Amsterdam: 1981.

<A NAME="RE28810SS-98">98</A> Brown HC. Khire UR. Narla G. Racherla US. J. Org. Chem. 1995, 60: 544

<A NAME="RE28810SS-99">99</A> Gonzalez AZ. Soderquist JA. Org. Lett. 2007, 9: 1081

<A NAME="RE28810SS-100">100</A> For further details on this reaction, see: Canales E. Gonzalez AZ. Soderquist JA. Angew. Chem. Int. Ed. 2007, 46: 397 ; Angew. Chem. 2007, 119, 401

<A NAME="RE28810SS-101">101</A> Matteson DS. In Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine Hall DG. Wiley-VCH; Weinheim: 2005. p.305

<A NAME="RE28810SS-102">102</A> Kobayashi S. Kitanosono T. Ueno M. Synlett 2010, 2033

<A NAME="RE28810SS-103">103</A> Fandrick DR. Johnson CS. Fandrick KR. Reeves JT. Tan Z. Lee H. Song JJ. Yee NK. Senanayake C. Org. Lett. 2010, 12: 748