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miyaura borylation wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 scope 2 see also 3 references toggle the table of contents miyaura borylation 3 languages čeština فارسی 한국어 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction miyaura borylation named after norio miyaura reaction type organic redox reaction identifiers organic chemistry portal miyaura borylation reaction miyaura borylation also known as the miyaura borylation reaction is a named reaction in organic chemistry that allows for the generation of boronates from vinyl or aryl halides with the cross coupling of bis pinacolato diboron in basic conditions with a catalyst such as pdcl 2 dppf the resulting borylated products can be used as coupling partners for the suzuki reaction 1 scope edit the miyaura borylation has shown to work for alkyl halides 2 aryl halides 1 3 4 aryl halides using tetrahydroxydiboron 5 aryl halides using bis boronic acid 6 aryl triflates 7 aryl mesylates 8 vinyl halides 9 vinyl halides of α β unsaturated carbonyl compounds 10 and vinyl triflates 11 see also edit chan lam coupling heck reaction hiyama coupling kumada coupling negishi coupling petasis reaction sonogashira coupling stille reaction suzuki reaction list of organic reactions references edit 1 2 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 hdl 2115 56184 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 hdl 2115 14605 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 retrieved from https en wikipedia org w index php title miyaura_borylation oldid 1316904113 category name reactions hidden categories articles with short description short description matches wikidata this page was last edited on 15 october 2025 at 04 06 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents miyaura borylation 3 languages add topic