- Seeking structural repetitivity in systems with interaction interference: Crystal engineering in the gem-alkynol family
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Synthon repetitivity has been demonstrated in a pair of gem-alkynols, despite the high degree of interaction interference typical of this family of compounds.
- Madhavi, N.N. Laxmi,Bilton, Clair,Howard, Judith A.K.,Allen, Frank H.,Nangia, Ashwini,Desiraju, Gautam R.
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- Alkoxyboration: Ring-closing addition of B-O σ bonds across alkynes
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For nearly 70 years, the addition of boron-X σ bonds to carbon-carbon multiple bonds has been employed in the preparation of organoboron reagents. However, the significantly higher strength of boron-oxygen bonds has thus far precluded their activation for addition, preventing a direct route to access a potentially valuable class of oxygen-containing organoboron reagents for divergent synthesis. We herein report the realization of an alkoxyboration reaction, the addition of boron-oxygen σ bonds to alkynes. Functionalized O-heterocyclic boronic acid derivatives are produced using this transformation, which is mild and exhibits broad functional group compatibility. Our results demonstrate activation of this boron-O σ bond using a gold catalysis strategy that is fundamentally different from that used previously for other boron addition reactions.
- Hirner, Joshua J.,Faizi, Darius J.,Blum, Suzanne A.
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supporting information
p. 4740 - 4745
(2014/04/17)
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- Synthesis of buta-1,3-diyne-bridged macrocycles with (Z)-1,4-diethynyl-1,4-dimethoxycyclohexa-2,5-diene as the building block
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(Z)-1,4-Diethynyl-1,4-dimethoxycyclohexa-2,5-diene has been used as a building block for the synthesis of two novel macrocycles containing buta-1,3-diyne units as bridges. The tetrayne derivative 5c has been structurally characterized by single crystal X-ray crystallographic data. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Srinivasan, Manivannan,Sankararaman, Sethuraman,Hopf, Henning,Varghese, Babu
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p. 660 - 665
(2007/10/03)
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