بوریلاسیون میائورا

بوریلاسیون میائورا
نامگذاری شده پس از	نوریو میائورا
نوع واکنش	اکسایش و کاهش آلی
شناسه‌ها
در درگاه شیمی آلی	miyaura-borylation-reaction

بوریلاسیون میائورا (به انگلیسی: Miyaura borylation) که به عنوان واکنش بوریلاسیون میائورا نیز شناخته می‌شود، یک نام واکنش در شیمی آلی است که امکان تولید بورونات‌ها از وینیل یا آریل هالیدها را با جفت شدن متقابل بیس(پیناکولاتو)دی‌بور در شرایط بازی با کاتالیزوری مانند PdCl₂(dppf) فراهم می‌کند. محصولات بوریله به دست آمده را می‌توان به عنوان شرکای جفت‌کننده برای واکنش سوزوکی استفاده کرد.^[۱]

گستره ویرایش

مشخص شده‌است که بوریلاسیون میائورا در موارد زیر کاربرد دارد:

آلکیل هالیدها،^[۲] آریل هالیدها،^[۱]^[۳]^[۴] آریل هالیدها با استفاده از تتراهیدروکسی‌دی بور،^[۵] آریل هالیدها با استفاده از بیس-بورونیک اسید،^[۶] آریل تری‌فلات،^[۷] آریل مسیلات‌ها،^[۸] وینیل هالیدها،^[۹] وینیل هالیدهای ترکیبات کربونیل غیراشباع β، α^[۱۰] و تری‌فلات وینیل‌ها.^[۱۱]

جستارهای وابسته ویرایش

منابع ویرایش

↑ ^۱٫۰ ^۱٫۱ Ishiyama, Tatsuo; Murata, Miki; Miyaura, Norio (1 November 1995). "Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters". The Journal of Organic Chemistry. 60 (23): 7508–7510. doi:10.1021/jo00128a024.
↑ Dudnik, Alexander S.; Fu, Gregory C. (6 June 2012). "Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds". J. Am. Chem. Soc. 134 (25): 10693–10697. doi:10.1021/ja304068t. PMC 3384763. PMID 22668072.
↑ Rao, Kanusu Umamaheswara; Ventateswarlu, Katta (16 March 2018). "PdII-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation". Synlett. 29 (8): 1055–1060. doi:10.1055/s-0036-1591549.
↑ Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. (18 March 2011). "Efficient Monophosphorus Ligands for Palladium-Catalyzed Miyaura Borylation". Organic Letters. 13 (6): 1366–1369. doi:10.1021/ol2000556. PMID 21319836.
↑ Molander, Gary A.; Trice, Sarah L. J.; Dreher, Spencer D. (24 November 2010). "Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives". Journal of the American Chemical Society. 132 (50): 17701–17703. doi:10.1021/ja1089759. PMC 3075417. PMID 21105666.
↑ Molander, Gary A.; Trice, Sarah L. J.; Kennedy, Steven M. (20 September 2012). "Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid". The Journal of Organic Chemistry. 77 (19): 8678–8688. doi:10.1021/jo301642v. PMC 3465529. PMID 22994557.
↑ Thompson, Alicia L. S.; Kabalka, George W.; Akula, Murthy R.; Huffman, John W. (18 January 2005). "The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions". Synthesis. 2005 (4): 547–550. doi:10.1055/s-2005-861791.
↑ Molander, Gary A.; Cavalcanti, Livia N.; García-García, Caraolina (18 June 2013). "Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B2(OH)4]". The Journal of Organic Chemistry. 78 (13): 6427–6439. doi:10.1021/jo401104y. PMC 3740274. PMID 23777538.
↑ Takahashi, Kou; Takagi, Jun; Ishiyama, Tatsuo; Miyaura, Norio (February 2000). "1-Alkenylboronic acid pinacol esters can be synthesized via a palladium-catalyzed cross-coupling reaction of 1-alkenyl halides or triflates with bis(pinacolato)diboron in toluene at 50°C in the presence of potassium phenoxide and PdCl2(PPh3)2·2PPh3". Chemistry Letters. 29 (2): 126–127. doi:10.1246/cl.2000.126. {{cite journal}}: |hdl-access= requires |hdl= (help)
↑ Takagi, Jun; Kamon, Akahiro; Ishiyama, Tatsuo; Miyaura, Norio (November 2002). "Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates". Synlett. 2002 (11): 1880–1882. doi:10.1055/s-2002-34869. {{cite journal}}: |hdl-access= requires |hdl= (help)
↑ Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura (17 June 2002). "Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides or Triflates: Convenient Synthesis of Unsymmetrical 1,3-Dienes via the Borylation-Coupling Sequence". Journal of the American Chemical Society. 124 (27): 8001–8006. doi:10.1021/ja0202255. PMID 12095344.

[Miyaura-1] ۱٫۰ ^۱٫۱ Ishiyama, Tatsuo; Murata, Miki; Miyaura, Norio (1 November 1995). "Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters". The Journal of Organic Chemistry. 60 (23): 7508–7510. doi:10.1021/jo00128a024.

[2] Dudnik, Alexander S.; Fu, Gregory C. (6 June 2012). "Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds". J. Am. Chem. Soc. 134 (25): 10693–10697. doi:10.1021/ja304068t. PMC 3384763. PMID 22668072.

[3] Rao, Kanusu Umamaheswara; Ventateswarlu, Katta (16 March 2018). "PdII-Porphyrin Complexes - the First Use as Safer and Efficient Catalysts for Miyaura Borylation". Synlett. 29 (8): 1055–1060. doi:10.1055/s-0036-1591549.

[4] Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. (18 March 2011). "Efficient Monophosphorus Ligands for Palladium-Catalyzed Miyaura Borylation". Organic Letters. 13 (6): 1366–1369. doi:10.1021/ol2000556. PMID 21319836.

[5] Molander, Gary A.; Trice, Sarah L. J.; Dreher, Spencer D. (24 November 2010). "Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives". Journal of the American Chemical Society. 132 (50): 17701–17703. doi:10.1021/ja1089759. PMC 3075417. PMID 21105666.

[6] Molander, Gary A.; Trice, Sarah L. J.; Kennedy, Steven M. (20 September 2012). "Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid". The Journal of Organic Chemistry. 77 (19): 8678–8688. doi:10.1021/jo301642v. PMC 3465529. PMID 22994557.

[7] Thompson, Alicia L. S.; Kabalka, George W.; Akula, Murthy R.; Huffman, John W. (18 January 2005). "The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions". Synthesis. 2005 (4): 547–550. doi:10.1055/s-2005-861791.

[8] Molander, Gary A.; Cavalcanti, Livia N.; García-García, Caraolina (18 June 2013). "Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B2(OH)4]". The Journal of Organic Chemistry. 78 (13): 6427–6439. doi:10.1021/jo401104y. PMC 3740274. PMID 23777538.

[9] Takahashi, Kou; Takagi, Jun; Ishiyama, Tatsuo; Miyaura, Norio (February 2000). "1-Alkenylboronic acid pinacol esters can be synthesized via a palladium-catalyzed cross-coupling reaction of 1-alkenyl halides or triflates with bis(pinacolato)diboron in toluene at 50°C in the presence of potassium phenoxide and PdCl2(PPh3)2·2PPh3". Chemistry Letters. 29 (2): 126–127. doi:10.1246/cl.2000.126. {{cite journal}}: |hdl-access= requires |hdl= (help)

[10] Takagi, Jun; Kamon, Akahiro; Ishiyama, Tatsuo; Miyaura, Norio (November 2002). "Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates". Synlett. 2002 (11): 1880–1882. doi:10.1055/s-2002-34869. {{cite journal}}: |hdl-access= requires |hdl= (help)

[11] Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura (17 June 2002). "Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides or Triflates: Convenient Synthesis of Unsymmetrical 1,3-Dienes via the Borylation-Coupling Sequence". Journal of the American Chemical Society. 124 (27): 8001–8006. doi:10.1021/ja0202255. PMID 12095344.

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