Regiospecific Conversion of 3,4‐Bis(trimethylsilyl)furan to 3,4‐Disubstituted Furans: A Novel Suzuki‐Type Cross‐Coupling of Boroxines

Song, Zhi Zhong; Zhou, Zhóng Yuan; Mak, Thomas C. W.; Wong, H. N. C.

doi:10.1002/anie.199304321

Cited by 41 publications

(5 citation statements)

References 41 publications

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“…The BÐO bond lengths in (I) range from 1.376 (3) to 1.397 (3) A Ê , with an average value of 1.384 A Ê . Very similar BÐO bond lengths, with an average of 1.381 A Ê , have been reported for other boroxines (Boese et al, 1987;Brock et al, 1987;Satoh & Cheng, 1994;Beckett et al, 1997;Song et al, 1993;Avent et al, 1990). The BÐN bond lengths in (II) range from 1.423 (6) to 1.442 (7) A Ê , with an average value of 1.431 A Ê .…”

Section: Commentsupporting

confidence: 77%

Isomorphism and phase transition in triferrocenylboroxine and triferrocenylborazine

Bats

2002

Acta Crystallogr C

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The crystal structures of triferrocenylboroxine, [Fe(3)(C(5)H(5))(3)(C(15)H(12)B(3)O(3))], (I), and triferrocenylborazine, [Fe(3)(C(5)H(5))(3)(C(15)H(15)B(3)N(3))], (II), are isomorphous. At room temperature, the space group is Cmc2(1) and the molecules have crystallographic m symmetry. A reversible phase transition occurs at 283(2)K for (I) and at 263(5)K for (II). In the low-temperature phase, the space group of both compounds is P2(1) and the molecules no longer have internal symmetry. Intermolecular C-H...pi interactions are enhanced in the low-temperature phase.

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Section: Commentsupporting

confidence: 77%

Isomorphism and phase transition in triferrocenylboroxine and triferrocenylborazine

Bats

2002

Acta Crystallogr C

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“…The pressure-induced acceleration allows the temperature to be lowered, that leads to a further increase in diastereoselectivity. The Diels-Alder reactions of unreactive dienes such as pyrazole [52 -54] and oxazole [55] derivatives (Scheme 12, entry (4) - (7)) are accelerated by high pressure which allows the temperature of reaction to be lowered so that the thermally labile cycloadducts and the 3,4-di-(trimethylsilyl)furan, respectively, can be isolated. The Effect of Pressure on Organic Reactions…”

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confidence: 99%

The Effect of Pressure on Organic Reactions

Klärner¹,

Wurche²

2000

J. prakt. Chem.

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The utility of high pressure for the understanding of chemical reactions and its application in organic synthesis is shown for cycloadditions (inter‐ and intramolecular Diels‐Alder reactions, 1,3‐dipolar and [2+2] cycloadditions), cheletropic reactions and pericyclic rearrangements (Cope and Claisen rearrangements and electrocyclizations). The origin of the effect of pressure on chemical reactions is discussed. Especially, the change in the packing coefficient during cyclization of chains and the effect of electrostriction on reactions, in which charged species are generated, contribute substantially to a volume contraction leading to a powerful pressure‐induced acceleration of such reactions. Finally, the effect of pressure on free‐radical reactions (homolytic bond dissociations and quinone oxidations) is described.

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“…Wong has extended this chemistry by developing a route to the preparation of 3,4-disubstituted furans starting with 42 by performing two successive sequences. 24,25 The first reaction of each sequence was an ipso-substitution with one equivalent of BCl 3 to provide boroxine 44 in 98% yield (Scheme 11). The second reaction in the sequence was a Suzuki coupling between 44 and a variety of aryl and heteroaryl halides to provide 45.…”

Section: The Role Of Silyl Groups On Furan Ringsmentioning

confidence: 99%

Synthesis of multi-substituted furan rings: the role of silicon

Keay¹

1999

Chem. Soc. Rev.

196

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Silanes have proven extremely useful for the synthesis of multi-substituted furan rings. Their judicious placement on a furan ring can be used to control either the placement of new groups around the furan ring or the silane can be directly replaced via an ipso-substitution. This paper will briefly review the role silicon has played in the preparation of furan rings having a variety of substituent patterns. replaced by electrophiles via an z/wo-substitution. In addition, their size has had a pronounced influence on the regioselectivity for introduction of other groups on the furan ring and on some rearrangements. This paper will briefly review the role organosilyl groups have played in the synthesis of multisubstituted furan rings. This will not be an exhaustive review, but will concentrate on how silyl groups have been used to prepare specific substitution patterns with furan rings.

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Regiospecific Conversion of 3,4‐Bis(trimethylsilyl)furan to 3,4‐Disubstituted Furans: A Novel Suzuki‐Type Cross‐Coupling of Boroxines

Abstract: 364.[9] The C1S meso protons and other protons cannot be assigned becduse of overlap between b = 0 and 6 = 4 of the NMR spectra of 1.2, and solvent.

Cited by 41 publications

References 41 publications

Isomorphism and phase transition in triferrocenylboroxine and triferrocenylborazine

Isomorphism and phase transition in triferrocenylboroxine and triferrocenylborazine

The Effect of Pressure on Organic Reactions

Synthesis of multi-substituted furan rings: the role of silicon

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