Suzuki coupling of aroyl-MIDA boronate esters – A preliminary report on scope and limitations

Lai, Samson; Takaesu, Noah; Lin, Wen Xuan; Perrin, David M.

doi:10.1016/j.tetlet.2021.153147

Cited by 3 publications

(1 citation statement)

References 57 publications

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“…68 Besides, there are several more reports, where the MIDA moiety was utilized as a coupling partner in SM coupling reactions to synthesize various biologically active compounds. 69…”

Section: Functionalization Of Substituted Mida Boronatesmentioning

confidence: 99%

Recent advances in the synthesis and reactivity of MIDA boronates

et al. 2022

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“…68 Besides, there are several more reports, where the MIDA moiety was utilized as a coupling partner in SM coupling reactions to synthesize various biologically active compounds. 69…”

Section: Functionalization Of Substituted Mida Boronatesmentioning

confidence: 99%

Recent advances in the synthesis and reactivity of MIDA boronates

et al. 2022

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Catalytic Asymmetric Transfer Hydrogenation of Acylboronates: BMIDA as the Privileged Directing Group

Meng,

Lan,

Chen

et al. 2024

J. Am. Chem. Soc.

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Developing a general, highly efficient, and enantioselective catalytic method for the synthesis of chiral alcohols is still a formidable challenge. We report in this article the asymmetric transfer hydrogenation (ATH) of N-methyliminodiacetyl (MIDA) acylboronates as a general substrate-independent entry to enantioenriched secondary alcohols. ATH of acyl-MIDA-boronates with (het)aryl, alkyl, alkynyl, alkenyl, and carbonyl substituents delivers a variety of enantioenriched α-boryl alcohols. The latter are used in a range of stereospecific transformations based on the boron moiety, enabling the synthesis of carbinols with two closely related α-substituents, which cannot be obtained with high enantioselectivities using direct asymmetric hydrogenation methods, such as the (R)-cloperastine intermediate. Computational studies illustrate that the BMIDA group is a privileged enantioselectivity-directing group in Noyori−Ikariya ATH compared to the conventionally used aryl and alkynyl groups due to the favorable CH−O attractive electrostatic interaction between the η 6 -arene-CH of the catalyst and the σ-bonded oxygen atoms in BMIDA. The work expands the domain of conventional ATH and shows its huge potential in addressing challenges in symmetric synthesis.

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Suzuki–Miyaura cross-couplings for alkyl boron reagent: recent developments—a review

Ahmed,

Mushtaq,

Chinnam

2023

Futur J Pharm Sci

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In the history of catalysis and organic synthesis, boric chemistry has been developed into one of the most varied and practical disciplines. Several useful Suzuki–Miyaura cross-coupling (SMC) reactions as well as hydroborylation reactions are regarded the essential tools inside the chemical synthesis toolkit accompanied by researchers of the industry or the academia. Novel synthesis of the less electrically and sterically ongoing carbon–boron synthetic reagents is carried out to ensure a unique coupling reaction utilizing metals along with these reagents which draws considerable interest in accelerating the discovery of creative uses for otherwise difficult organic adducts in many disciplines. This article details the noteworthy advancements in the use of traditional metal-catalyzed carbon–carbon coupling processes with cutting-edge coupling partners such as carbon–boron reagents often the beta-alkyl Suzuki–Miyaura coupling since 2001. The current review covers alkylboranes, organotrifluoroborates, 9-BBN, alkylboronic acids and boronic esters as useful reagents in SMCs that will help synthetic chemists in developing new compounds. Graphical Abstract

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Suzuki coupling of aroyl-MIDA boronate esters – A preliminary report on scope and limitations

Cited by 3 publications

References 57 publications

Recent advances in the synthesis and reactivity of MIDA boronates

Recent advances in the synthesis and reactivity of MIDA boronates

Catalytic Asymmetric Transfer Hydrogenation of Acylboronates: BMIDA as the Privileged Directing Group

Suzuki–Miyaura cross-couplings for alkyl boron reagent: recent developments—a review

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