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Palladium-catalyzed regio- and enantioselective migratory allylic C(sp3)-H functionalization
被引:41
作者:

Chen, Ye-Wei
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Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China
ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai, Peoples R China Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China

Liu, Yang
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Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China

Lu, Han-Yu
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Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China
ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai, Peoples R China Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China

Lin, Guo-Qiang
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Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China
ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai, Peoples R China Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China

He, Zhi-Tao
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Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China
机构:
[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, Shanghai, Peoples R China
[2] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai, Peoples R China
基金:
中国国家自然科学基金;
关键词:
C-H OXIDATION;
NONCONJUGATED DIENES;
TERMINAL OLEFINS;
ASYMMETRIC-SYNTHESIS;
WALKING METALS;
ARYL IODIDES;
HYDROAMINATION;
AMINES;
ACID;
SUBSTITUTION;
D O I:
10.1038/s41467-021-25978-6
中图分类号:
O [数理科学和化学];
P [天文学、地球科学];
Q [生物科学];
N [自然科学总论];
学科分类号:
07 ;
0710 ;
09 ;
摘要:
Transition metal-catalyzed asymmetric allylic substitution with a suitably pre-stored leaving group in the substrate is widely used in organic synthesis. In contrast, the enantioselective allylic C(sp(3))-H functionalization is more straightforward but far less explored. Here we report a catalytic protocol for the long-standing challenging enantioselective allylic C(sp(3))-H functionalization. Through palladium hydride-catalyzed chain-walking and allylic substitution, allylic C-H functionalization of a wide range of acyclic nonconjugated dienes is achieved in high yields (up to 93% yield), high enantioselectivities (up to 98:2 er), and with 100% atom efficiency. Exploring the reactivity of substrates with varying pK(a) values uncovers a reasonable scope of nucleophiles and potential factors controlling the reaction. A set of efficient downstream transformations to enantiopure skeletons showcase the practical value of the methodology. Mechanistic experiments corroborate the PdH-catalyzed asymmetric migratory allylic substitution process. Alkene isomerizations and asymmetric C-H functionalizations have been independently studied, but their combination in one protocol is uncommon. Here the authors show a palladium-catalyzed method to iteratively "walk" a terminal alkene along a carbon chain to a position next to styrenes where a soft nucleophile is added asymmetrically.
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页数:9
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