Enantioselective Addition of Pyrazoles to Dienes**

Alexander Y. Jiu; Hannah S. Slocumb; Charles S. Yeung; Xiao Hui Yang; Vy M. Dong

doi:10.1002/anie.202105679

Enantioselective Addition of Pyrazoles to Dienes**

Alexander Y. Jiu
, Hannah S. Slocumb
, Charles S. Yeung
, Xiao Hui Yang^*
, Vy M. Dong^*

^*Corresponding author for this work

University of California at Irvine
Merck
Beijing Institute of Technology

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

96 Citations (Scopus)

Abstract

We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd⁰-catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.

Original language	English
Pages (from-to)	19660-19664
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	36
DOIs	https://doi.org/10.1002/anie.202105679
Publication status	Published - 1 Sept 2021
Externally published	Yes

Keywords

1,3-diene
Pd-catalysis
enantioselectivity
hydroamination
pyrazole

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10.1002/anie.202105679

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abstract = "We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd0-catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.",

keywords = "1,3-diene, Pd-catalysis, enantioselectivity, hydroamination, pyrazole",

author = "Jiu, \{Alexander Y.\} and Slocumb, \{Hannah S.\} and Yeung, \{Charles S.\} and Yang, \{Xiao Hui\} and Dong, \{Vy M.\}",

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T1 - Enantioselective Addition of Pyrazoles to Dienes**

AU - Jiu, Alexander Y.

AU - Slocumb, Hannah S.

AU - Yeung, Charles S.

AU - Yang, Xiao Hui

AU - Dong, Vy M.

PY - 2021/9/1

Y1 - 2021/9/1

N2 - We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd0-catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.

AB - We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd0-catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.

KW - 1,3-diene

KW - Pd-catalysis

KW - enantioselectivity

KW - hydroamination

KW - pyrazole

UR - https://www.scopus.com/pages/publications/85111688807

U2 - 10.1002/anie.202105679

DO - 10.1002/anie.202105679

M3 - Article

C2 - 34145705

AN - SCOPUS:85111688807

SN - 1433-7851

VL - 60

SP - 19660

EP - 19664

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 36

ER -

Enantioselective Addition of Pyrazoles to Dienes**

Abstract

Keywords

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