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Regio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Brà̧nsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan by Liu, Xiaocui; Ming, Wenbo; Luo, Xiaoling; Friedrich, Alexandra; Maier, Jan; Radius, Udo; Santos, Webster L.; Marder, Todd B. is a Chemistry article available to read on EtoBox.

What is Regio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Brà̧nsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan about?

The NaO__t__Bu‐catalyzed mixed 1,1‐diboration of terminal alkynes using the unsymmetrical diboron reagent BpinBdan (pin = pinacolato; dan = 1,8‐diaminonaphthalene) proceeds in a regio‐ and stereoselective fashion affording moderate to high yields of 1,1‐diborylalkenes bearing orthogonal boron protecting groups. It is applicable to gram‐scale synthesis without loss of yield or selectivity. The mixed 1,1‐diborylalkene products can be utilized in Suzuki–Miyaura cross‐coupling reactions which take place selectivly at the C–B site. DFT calculations suggest the NaO__t__Bu‐catalyzed mixed 1,1‐diboration of alkynes occurs through deprotonation of the terminal alkyne, stepwise addition of BpinBdan to the terminal carbon followed by protonation with __t__BuOH. Experimentally observed selective formation of (__Z__)‐diborylalkenes is supported by our theoretical studies.

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Author

Liu, Xiaocui; Ming, Wenbo; Luo, Xiaoling; Friedrich, Alexandra; Maier, Jan; Radius, Udo; Santos, Webster L.; Marder, Todd B.

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1434-193X)

Published

2020

Language

EN

Field

Chemistry (Physical Sciences)