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Lipase-catalyzed esterification in water enabled by nanomicelles. Applications to 1-pot multi-step sequences

https://doi.org/10.1039/d1sc05660c

Singhania, Vani; Cortes-Clerget, Margery; Dussart-Gautheret, Jade; Akkachairin, Bhornrawin; Yu, Julie; Akporji, Nnamdi; Gallou, Fabrice; Lipshutz, Bruce H. (February 2022, Chemical Science)

Esterification in an aqueous micellar medium is catalyzed by a commercially available lipase in the absence of any co-factors. The presence of only 2 wt% designer surfactant, TPGS-750-M, assists in a 100% selective enzymatic process in which only primary alcohols participate (in a 1 : 1 ratio with carboxylic acid). An unexpected finding is also disclosed where the simple additive, PhCF 3 (1 equiv. vs. substrate), appears to significantly extend the scope of usable acid/alcohol combinations. Taken together, several chemo- and bio-catalyzed 1-pot, multi-step reactions can now be performed in water.
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Continuous flow Suzuki–Miyaura couplings in water under micellar conditions in a CSTR cascade catalyzed by Fe/ppm Pd nanoparticles

https://doi.org/10.1039/d0gc00378f

Wood, Alex B.; Nandiwale, Kakasaheb Y.; Mo, Yiming; Jin, Bo; Pomberger, Alexander; Schultz, Victor L.; Gallou, Fabrice; Jensen, Klavs F.; Lipshutz, Bruce H. (June 2020, Green Chemistry)

The first demonstration of aqueous surfactant-enabled Suzuki–Miyaura couplings run under flow conditions is described. In addition, use of an even more challenging heterogeneous nanoparticle catalyst, containing only 800 ppm of Pd ( i.e. , 0.08 mol%) in the form of Fe/ppm Pd nanoparticles, is sufficient using a continuous stirred-tank reactor (CSTR).
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A Sustainable 1-Pot, 3-Step Synthesis of Boscalid Using Part per Million Level Pd Catalysis in Water

https://doi.org/10.1021/acs.oprd.9b00455

Takale, Balaram S.; Thakore, Ruchita R.; Mallarapu, Rushil; Gallou, Fabrice; Lipshutz, Bruce H. (January 2020, Organic Process Research & Development)

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An environmentally responsible 3-pot, 5-step synthesis of the antitumor agent sonidegib using ppm levels of Pd catalysis in water

https://doi.org/10.1039/c9gc03495a

Takale, Balaram S.; Thakore, Ruchita R.; Kong, Fan Yi; Lipshutz, Bruce H. (November 2019, Green Chemistry)

The current industrial approach to sonidegib utilizes wasteful organic solvents and relies on high loadings of endangered Pd. This anticancer drug can now be synthesized in 5 steps using only 3 pots, along with ppm levels of a Pd catalyst, all done in water at ambient temperatures.
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N , C -Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions

https://doi.org/10.1021/acscatal.9b04204

Thakore, Ruchita R.; Takale, Balaram S.; Gallou, Fabrice; Reilly, John; Lipshutz, Bruce H. (October 2019, ACS Catalysis)

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