Extremely electron-rich, boron-functionalized, icosahedral carborane-based phosphinoboranes

Alexander M. Spokoyny; Calvin D. Lewis; Georgiy Teverovskiy; Stephen L. Buchwald

doi:10.1021/om301116x

Extremely electron-rich, boron-functionalized, icosahedral carborane-based phosphinoboranes

Alexander M. Spokoyny, Calvin D. Lewis, Georgiy Teverovskiy, Stephen L. Buchwald

Division of Cancer Biology

Research output: Contribution to journal › Article › peer-review

102 Scopus citations

Abstract

We have prepared the first examples of B9-connected trivalent aryl and alkyl phosphinoborane species via Pd-catalyzed phosphination of 9-iodo-meta-carborane. Our studies highlight the unique electronic features of the B9-connected meta-carboranyl moiety as compared to its C1-based analogue. This work suggests that the B9-functionalized meta-carboranyl substituent in these ligands exhibits more electron-releasing character than any other known carbon-based substituent, ultimately laying the foundation for a new class of phosphine ligands with extremely electron-rich character.

Original language	English
Pages (from-to)	8478-8481
Number of pages	4
Journal	Organometallics
Volume	31
Issue number	24
DOIs	https://doi.org/10.1021/om301116x
State	Published - Dec 24 2012

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AU - Spokoyny, Alexander M.

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AU - Teverovskiy, Georgiy

AU - Buchwald, Stephen L.

PY - 2012/12/24

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AB - We have prepared the first examples of B9-connected trivalent aryl and alkyl phosphinoborane species via Pd-catalyzed phosphination of 9-iodo-meta-carborane. Our studies highlight the unique electronic features of the B9-connected meta-carboranyl moiety as compared to its C1-based analogue. This work suggests that the B9-functionalized meta-carboranyl substituent in these ligands exhibits more electron-releasing character than any other known carbon-based substituent, ultimately laying the foundation for a new class of phosphine ligands with extremely electron-rich character.

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Extremely electron-rich, boron-functionalized, icosahedral carborane-based phosphinoboranes

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