Amphoteric alpha-Boryl Aldehyde Linchpins in the Synthesis of Heterocycles

作者：St Denis Jeffrey D; He Zhi; Yudin Andrei K^*

来源：ACS Catalysis, 2015, 5(9): 5373-5379.

DOI：10.1021/acscatal.5b00790

• transition metal catalysis
• boron
• amphoteric molecules
• organocatalysis
• heterocycle synthesis
• Suzuki-Miyaura cross-coupling

Pairing of mutually reactive functional groups in the same molecule affords enabling opportunities in chemical synthesis. Kinetically amphoteric molecules exemplify this scenario and help avoid the pitfalls of protecting-group chemistry by exploiting the innate reactivity of the functional groups. In this perspective, we highlight the recent development of MIDA (N-methyliminodiacetyl) alpha-boryl aldehydes as amphoteric building blocks that act as linchpins in the synthesis of heterocycles. This short review includes topics ranging from metal-catalyzed cyclization involving B-C-Pd intermediates to the intramolecular Suzuki-Miyaura cross-coupling that affords six- and seven-membered rings. The use of boryl aldehydes in other transformations, including halogenation and oxidation protocols, is also discussed.

• 出版日期2015-9