Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings

methyliminodiacetic acid (MIDA) boronates;organic synthesis;synthetic methods;Suzuki-Miyaura;Chan-Lam;iterative cross-coupling;Csp3-halide

Klubnick, Jenna A. ; Burke ; Martin D.

关键词: methyliminodiacetic acid (MIDA) boronates;    organic synthesis;    synthetic methods;    Suzuki-Miyaura;    Chan-Lam;    iterative cross-coupling;    Csp3-halide;   

Others  :  https://www.ideals.illinois.edu/bitstream/handle/2142/26352/Klubnick_Jenna.pdf?sequence=1&isAllowed=y

美国|英语

来源: The Illinois Digital Environment for Access to Learning and Scholarship

【 摘 要 】

The iterative cross-coupling strategy for small molecule synthesis has been shown to be a powerful and effective method for the synthesis of small molecules.However, this strategy was limited by current methodological limitations.Therefore, we have extended the power and application of the iterative cross-coupling strategy by the development of several new methods compatible with the iterative cross-coupling platform.We report a mild Csp3 halide – Csp2boronic acid Suzuki-Miyaura cross-coupling method amenable to fine molecule synthesis.We also report a new method for the synthesis of MIDA boronates which are sensitive to current methods.Finally, we report the extension of the entire iterative cross coupling platform to the Chan-Lam coupling to form carbon-heteroatom bonds.