Catalytic Enantioselective Dehydrogenative Si-O Coupling to Access Chiroptical Silicon-Stereogenic Siloxanes and Alkoxysilanes

Zhu，Jiefeng1,2; Chen，Shuyou2; He，Chuan2

2021

10.1021/jacs.1c01106

Journal of the American Chemical Society   影响因子和分区

0002-7863

1520-5126

A rhodium-catalyzed enantioselective construction of triorgano-substituted silicon-stereogenic siloxanes and alkoxysilanes is developed. This process undergoes a direct intermolecular dehydrogenative Si-O coupling between dihydrosilanes with silanols or alocohols, giving access to a variety of highly functionalized chiral siloxanes and alkoxysilanes in decent yields with excellent stereocontrol, that significantly expand the chemical space of the silicon-centered chiral molecules. Further utility of this process was illustrated by the construction of CPL-active (circularly polarized luminescence) silicon-stereogenic alkoxysilane small organic molecules. Optically pure bis-alkoxysilane containing two silicon-stereogenic centers and three pyrene groups displayed a remarkable glum value with a high fluorescence quantum efficiency (glum = 0.011, φF = 0.55), which could have great potential application prospects in chiral organic optoelectronic materials.

SCI ; IC ; CCR ; EI

英语

NI论文

通讯

WOS:000641160700003

20211810292460

Enantioselectivity ; Molecules ; Optoelectronic devices ; Silicon ; Stereochemistry

Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Optical Devices and Systems:741.3 ; Chemistry:801 ; Physical Chemistry:801.4 ; Atomic and Molecular Physics:931.3

2-s2.0-85104276012

Scopus

1.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150080,China
2.Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China

Zhu，Jiefeng,Chen，Shuyou,He，Chuan. Catalytic Enantioselective Dehydrogenative Si-O Coupling to Access Chiroptical Silicon-Stereogenic Siloxanes and Alkoxysilanes[J]. Journal of the American Chemical Society,2021,143:5301-5307.

Zhu，Jiefeng,Chen，Shuyou,&He，Chuan.(2021).Catalytic Enantioselective Dehydrogenative Si-O Coupling to Access Chiroptical Silicon-Stereogenic Siloxanes and Alkoxysilanes.Journal of the American Chemical Society,143,5301-5307.

Zhu，Jiefeng,et al."Catalytic Enantioselective Dehydrogenative Si-O Coupling to Access Chiroptical Silicon-Stereogenic Siloxanes and Alkoxysilanes".Journal of the American Chemical Society 143(2021):5301-5307.