Rhodium(I) catalysed diboration of (E)-styrylboronate esters: molecular structures of (E)-p-MeO–C6H4–CHCH–B(1,2-O2C6H4) and p-MeO–C6H4–CH2C{B(1,2-O2C6H4)}3

Nguyen, Paul; Coapes, R. Benjamin; Woodward, Alden; Taylor, Nicholas J.; Burke, Jacquelyn M.; Howard, Judith A. K.; Marder, Todd B.

doi:10.1016/s0022-328x(02)01310-4

Cited by 104 publications

(31 citation statements)

References 55 publications

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“…[14b, d, 15] Therefore, we soughtt od evelop an ew iron b-diketiminate complex that has enhanced electronic and steric properties, whichm ay proffer more favourable reactivity than the simple 2,6-diisopropyl substituted system. [18] Other internal alkynes also react to give the Z-alkene product exclusively,heteroatomsare tolerated and high levelsofregioselectivity were obtained (Table 1, entries 10 to 13). [17] When 1b catalyzes the HB of styrene, only three hours are necessary to give ac omparable yield of HB product, but remarkably,t his subtle change in ligand structure gives av ast change in regioselectivity: good levels of Markovnikovs electivity were obtained (3a, Ta ble 1, entry 1).…”

mentioning

confidence: 99%

Iron‐Catalyzed Hydroboration: Unlocking Reactivity through Ligand Modulation

Espinal‐Viguri

Woof

Webster

2016

Chemistry A European J

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Iron-catalyzed hydroboration (HB) of alkenes and alkynes is reported. A simple change in ligand structure leads to an extensive change in catalyst activity. Reactions proceed efficiently over a wide range of challenging substrates including activated, unactivated and sterically encumbered motifs. Conditions are mild and do not require the use of reducing agents or other additives. Large excesses of borating reagent are not required, allowing control of chemo- and regioselectivity in the presence of multiple double bonds. Mechanistic insight reveals that the reaction is likely to proceed via a highly reactive iron hydride intermediate.

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mentioning

confidence: 99%

Iron‐Catalyzed Hydroboration: Unlocking Reactivity through Ligand Modulation

Espinal‐Viguri

Woof

Webster

2016

Chemistry A European J

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“…The B-O bond distances (avg. = 1.3955(5) Å) are also typical for three-coordinate Bcat groups (52)(53)(54)(55) and are significantly shorter than those observed in chelate complexes with diphenylborinic acid (ca. 1.5 Å), where the boron atom is four coordinate (56).…”

Section: Resultsmentioning

confidence: 82%

Synthesis and catalysed hydroboration of styryl sulfonamides

Wynberg¹,

Leger²,

Conrad³

et al. 2005

Can. J. Chem.

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We have prepared the aryl sulfonamides 4,4′ -R-C 6 H 4 SO 2 NHC 6 H 4 CH=CH 2 (R = CH 3 , 1a; NO 2 , 1b) by addition of 2 equiv. of 4-vinylaniline to the corresponding sulfonyl chlorides. The disulfonamides 4,4,4′ -(R-C 6 H 4 SO 2 ) 2 -NC 6 H 4 CH=CH 2 (R = CH 3 , 2a; NO 2 , 2b) were also prepared using 4-vinylaniline and 2 equiv. of the sulfonyl chlorides in the presence of DMAP. Although hydroborations of sulfanilamide derivatives 1 suffered from competing hydrogenation reactions, judicious choice of the transition metal catalyst gave selective formation of either the primary or secondary boronate esters in hydroborations of 2a.Résumé : On a préparé les aryl sulfonamides, 4,4′ -R-C 6 H 4 SO 2 NHC 6 H 4 CH=CH 2 (R = CH 3 , 1a; NO 2 , 1b) par l'addition de deux équivalents de 4-vinylaniline aux chlorures de sulfonyle correspondants. On a aussi préparé les disulfonamides 4,4,4′ -(R-C 6 H 4 SO 2 ) 2 NC 6 H 4 CH=CH 2 (R = CH 3 , 2a; NO 2 , 2b) à partir de la 4-vinylaniline et de deux équivalents de chlorures de sulfonyle, en présence de DMAP. Quoique les réactions d'hydroboration des dérivés sulfanilamides 1 soient en compétition avec les réactions d'hydrogénation, un choix judicieux d'un catalyseur à base d'un métal de transition permet d'obtenir la formation sélective des boronates soit primaires ou secondaires lors des hydroborations du composé 2a.Mots clés : esters de l'acide boronique, hydroborations catalysées, sulfanilamides, vinylaniline.[Traduit par la Rédaction] Wynberg et al.

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“…Terminal alkynes are very useful reagents in the synthesis of diverse organoboron compounds . In 1995, our group reported a Rh‐catalyzed 1,1‐diboration of ( E )‐styrylboronates prepared via hydroboration of the corresponding ethynylarenes with HBcat (HBcat=catecholborane; Scheme a), which yielded predominantly 1,1,1‐triboronates . In 2017, Chirik et al.…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Triboration: Straightforward, Atom‐Economical Synthesis of 1,1,1‐Triborylalkanes from Terminal Alkynes and HBpin

et al. 2019

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A convenient and efficient one‐step synthesis of 1,1,1‐triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroborations of terminal alkynes with HBpin (HBpin=pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)2. This process proceeds under mild conditions, furnishing 1,1,1‐tris(boronates) with wide substrate scope, excellent selectivity, and good functional‐group tolerance, and is applicable to gram‐scale synthesis without loss of yield. The 1,1,1‐triborylalkanes can be used in the preparation of α‐vinylboronates and borylated cyclic compounds, which are valuable but previously rare compounds. Different alkyl groups can be introduced stepwise via base‐mediated deborylative alkylation to produce racemic tertiary alkyl boronates, which can be readily transformed into useful tertiary alcohols.

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Rhodium(I) catalysed diboration of (E)-styrylboronate esters: molecular structures of (E)-p-MeO–C6H4–CHCH–B(1,2-O2C6H4) and p-MeO–C6H4–CH2C{B(1,2-O2C6H4)}3

Cited by 104 publications

References 55 publications

Iron‐Catalyzed Hydroboration: Unlocking Reactivity through Ligand Modulation

Iron‐Catalyzed Hydroboration: Unlocking Reactivity through Ligand Modulation

Synthesis and catalysed hydroboration of styryl sulfonamides

Copper‐Catalyzed Triboration: Straightforward, Atom‐Economical Synthesis of 1,1,1‐Triborylalkanes from Terminal Alkynes and HBpin

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