Investigations into ambient temperature biaryl coupling reactions

Anderson, James C.; Namlı, Hilmi; Roberts, Craig

doi:10.1016/s0040-4020(97)10010-2

Cited by 90 publications

(27 citation statements)

References 47 publications

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“…Hypothetically, this may be attributed to the sterically hindered triphenylphosphane-free, electron-rich Ni I metal center [41,42] (Figure 2a) compared to that of the low-valent ruthenium(II) center. This can be attributed to the efficiency of NiL, which facilitates a faster oxidative addition reaction in the catalytic cycle.…”

Section: Resultsmentioning

confidence: 99%

Expression of Concern: One‐Step Synthesis of Biaryls under Mild Conditions

Bhat

2013

Eur J Org Chem

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A one‐step synthesis of symmetrical biaryls was developed and uses a nickel(III) complex containing a Schiff base and dithiolate ligands as a catalyst for the homocoupling of in situ generated Grignard reagents. The coupling reaction was performed at room temperature with molecular oxygen as the oxidant, which renders the reaction energy‐efficient and environmentally friendly. The catalytic methodology is compatible with diverse functionalities, including chlorido, nitro, nitrile, and heteroatoms, and provides biaryls in appreciable yields.

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Section: Resultsmentioning

confidence: 99%

Expression of Concern: One‐Step Synthesis of Biaryls under Mild Conditions

Bhat

2013

Eur J Org Chem

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“…This sub-unit is fairly common, the best studied example being [Re 2 (CO) 8 (l-PPh 2 ) 2 ] [52,53], although here, and in all related complexes, there is no direct rhenium-rhenium contact [53]. Most closely related to 7 are carbene complexes [Re 2 (CO) 6 {@-CR 1 (OR 2 )} 2 (l-PPh 2 ) 2 ] (Chart 3) which also exist as a mixture of cis and trans isomers, the rhenium-carbon bond lengths being somewhat shorter [Re-C ca. 2.08-2.12 Å A 0 ] [54,55].…”

Section: Rementioning

confidence: 93%

“…Interest in the chemistry of tri(2-furyl)phosphine (PFu 3 ) stems from its potential to behave as a functionalized phosphine which has importance in transition metal catalysis [1][2][3][4][5][6][7][8]. Thus, it is well-known that heterodifunctional ligands show interesting properties such as selective binding to metal ions of different types, dynamic behavior via reversible dissociation of the weaker metalligand bond or stereoelectronic control of the coordination sphere of the metal [9].…”

Section: Introductionmentioning

confidence: 99%

Activation of tri(2-furyl)phosphine at a dirhenium centre: Formation of phosphido-bridged dirhenium complexes

Ghosh

Khatun

Haworth

et al. 2009

Journal of Organometallic Chemistry

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a b s t r a c tReaction of tri(2-furyl)phosphine (PFu 3 ) with [Re 2 (CO) 10Àn (NCMe) n ] (n = 1, 2) at 40°C gave the substituted complexes [Re 2 (CO) 10Àn (PFu 3 ) n ] (1 and 2), the phosphines occupying axial position in all cases. Heating [Re 2 (CO) 10 ] and PFu 3 in refluxing xylene also gives 1 and 2 together with four phosphido-bridged complexes; [Re 2 (CO) 8Àn (PFu 3 ) n (l-PFu 2 )(l-H)] (n = 0, 1, 2) (3-5) and [Re 2 (CO) 6 (PFu 3 ) 2 (l-PFu 2 )(l-Cl)] (6) resulting from phosphorus-carbon bond cleavage. A series of separate thermolysis experiments has allowed a detailed reaction pathway to be unambiguously established. A similar reaction between [Re 2 (CO) 10 ] and PFu 3 in refluxing chlorobenzene furnishes four complexes which include 1, 2, 6 and the new binuclear complex [Re 2 (CO) 6 (g 1 -C 4 H 3 O) 2 (l-PFu 2 ) 2 ] (7). All new complexes have been characterized by a combination of spectroscopic data and single crystal X-ray diffraction studies.

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“…Early methods required the use of toxic reagents, such as Tl compounds. 4 In recent years, a number of new ligands and reaction conditions have been developed, which allow to prepare sterically encumbered biaryls, such as 2,6-di-, 2,2 0 ,6-tri-and 2,2 0 ,6,6 0 -tetrasubstituted biaryls. This includes Suzuki-Miyaura and Stille reactions.…”

Section: Introductionmentioning

confidence: 99%

“…Hz, CH 3 ), 0.89 (t, 3H, 3 J¼7.5 Hz, CH 3 ), 2.09 (q, 2H, 3 J¼7.5 Hz, CH 2 ), 2.54 (q, 2H, 3 J¼7 4. Hz, CH 2 ), 5.29 (s, 2H, OCH 2 ), 6.72 (s, 1H, H Ar ),6.99-7.31 (m, 10H, 2Ph), 10.93 (s, 1H, OH);13 C NMR (75 MHz, CDCl 3 ): d¼14.5, 16.0 (CH 3 ), 25.6, 27.5 (CH 2 ), 67.6 (OCH 2 ), 109.9 (C Ar ), 114.7 (CH Ar ), 126.7 (CH Ph ), 128.1 (2CH Ph ), 128.6 (2CH Ph ), 128.7 (CH Ph ), 128.8 (2CH Ph ), 130.1 (2CH Ph ), 134.3,134.9,140.1,144.9,150.2,161.7 (C Ar ),171.4 (C]O); IR (KBr, cm À1 ):ñ ¼ 3027ðwÞ; 2965, 2878 (m), 1705 (w), 1644 (s), 1594, 1494, 1439, 1378 (m), 1311 (s),1254 (m),1212 (s),1174,1087,1035, 959, 880, 807 (m), 748, 705 (s), 654, 573 (m); MS (EI, 70 eV): m/z (%)¼361 (10), 360 (M þ , 46)Starting with 1,3-bis(silyl enol ether) 5a (600 mg, 2.30 mmol), 3-p-tolyl-4-(trimethylsilyloxy)pent-3-en-2-one 4c (603 mg, 2.30 mmol), and TiCl 4 (0.25 mL, 2.30 mmol), 6n was obtained as white solid (335 mg, 54%), mp¼112-114 C. 1 H NMR (300 MHz, CDCl 3 ): d¼1.98 (s, 3H, CH 3 ), 2.21 (s, 3H, CH 3 ), 2.42 (s, 3H, CH 3 ), 3.96 (s, 3H, OCH 3 ), 6.79 (s, 1H, H Ar ), 6.97 (br d, 2H, 3 J¼8.1 Hz, H Ar ), 7.21 (br d, 2H, 3 J¼8.1 Hz, H Ar ), 11.01 (s, 1H, OH); 13 C NMR (75 MHz, CDCl 3 ): d¼20.8, 21.2, 21.9 (CH 3 ), 52.0 (OCH 3 ),110.7 (C Ar ),116.1 (CH Ar ),129.2 (2CH Ar ),129.5 (2CH Ar ),135.1, 136.2, 137.7, 138.6, 144.2, 160.9 (C Ar ), 172.2 (C]O); IR (KBr, cm À1 )…”

mentioning

confidence: 99%