NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism

Fanke Meng; Byunghyuck Jung; Fredrik Haeffner; Amir H. Hoveyda

doi:10.1021/ol4004178

NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism

Fanke Meng
, Byunghyuck Jung
, Fredrik Haeffner
, Amir H. Hoveyda

Department of Physics and Chemistry

Boston College

Research output: Contribution to journal › Article › peer-review

96 Scopus citations

Abstract

Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.

Original language	English
Pages (from-to)	1414-1417
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	6
DOIs	https://doi.org/10.1021/ol4004178
State	Published - 15 Mar 2013

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title = "NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism",

abstract = "Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.",

author = "Fanke Meng and Byunghyuck Jung and Fredrik Haeffner and Hoveyda, \{Amir H.\}",

year = "2013",

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doi = "10.1021/ol4004178",

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journal = "Organic Letters",

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T1 - NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism

AU - Meng, Fanke

AU - Jung, Byunghyuck

AU - Haeffner, Fredrik

AU - Hoveyda, Amir H.

PY - 2013/3/15

Y1 - 2013/3/15

N2 - Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.

AB - Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.

UR - https://www.scopus.com/pages/publications/84875155048

U2 - 10.1021/ol4004178

DO - 10.1021/ol4004178

M3 - Article

C2 - 23461762

AN - SCOPUS:84875155048

SN - 1523-7060

VL - 15

SP - 1414

EP - 1417

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism

Abstract

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