TY - JOUR
T1 - Compartmentalization of Incompatible Catalytic Transformations for Tandem Catalysis
AU - Lu, Jie
AU - Dimroth, Jonas
AU - Weck, Marcus
PY - 2015/10/14
Y1 - 2015/10/14
N2 - In Nature, incompatible catalytic transformations are being carried out simultaneously through compartmentalization that allows for the combination of incompatible catalysts in tandem reactions. Herein, we take the compartmentalization concept to the synthetic realm and present an approach that allows two incompatible transition metal catalyzed transformations to proceed in one pot in tandem. The key is the site isolation of both catalysts through compartmentalization using a core-shell micellar support in an aqueous environment. The support is based on amphiphilic triblock copolymers of poly(2-oxazoline)s with orthogonal functional groups on the side chain that can be used to cross-link covalently the micelle and to conjugate two metal catalysts in different domains of the micelle. The micelle core and shell provide different microenvironments for the transformations: Co-catalyzed hydration of an alkyne proceeds in the hydrophobic core, while the Rh-catalyzed asymmetric transfer hydrogenation of the intermediate ketone into a chiral alcohol occurs in the hydrophilic shell.
AB - In Nature, incompatible catalytic transformations are being carried out simultaneously through compartmentalization that allows for the combination of incompatible catalysts in tandem reactions. Herein, we take the compartmentalization concept to the synthetic realm and present an approach that allows two incompatible transition metal catalyzed transformations to proceed in one pot in tandem. The key is the site isolation of both catalysts through compartmentalization using a core-shell micellar support in an aqueous environment. The support is based on amphiphilic triblock copolymers of poly(2-oxazoline)s with orthogonal functional groups on the side chain that can be used to cross-link covalently the micelle and to conjugate two metal catalysts in different domains of the micelle. The micelle core and shell provide different microenvironments for the transformations: Co-catalyzed hydration of an alkyne proceeds in the hydrophobic core, while the Rh-catalyzed asymmetric transfer hydrogenation of the intermediate ketone into a chiral alcohol occurs in the hydrophilic shell.
UR - http://www.scopus.com/inward/record.url?scp=84944262989&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84944262989&partnerID=8YFLogxK
U2 - 10.1021/jacs.5b07257
DO - 10.1021/jacs.5b07257
M3 - Article
C2 - 26426145
AN - SCOPUS:84944262989
VL - 137
SP - 12984
EP - 12989
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 40
ER -