Palladium-Catalyzed Norbornene-Mediated Tandem Amination/Cyanation Reaction: A Method for the Synthesis of ortho-Aminated Benzonitriles.
Luo, Bo; Gao, Jin-Ming; Lautens, Mark; Organic letters 18 (2016) 4166–4169; doi:10.1021/acs.orglett.6b02249

data_1555731
_publ_section_title
;
 Palladium-Catalyzed Norbornene-Mediated Tandem Amination/Cyanation
 Reaction: A Method for the Synthesis of ortho-Aminated Benzonitriles.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4166
_journal_page_last               4169
_journal_paper_doi               10.1021/acs.orglett.6b02249
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H21 N3 O2'
_chemical_formula_sum            'C16 H21 N3 O2'
_chemical_formula_weight         287.36
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                105.277(5)
_cell_angle_beta                 93.849(5)
_cell_angle_gamma                116.710(4)
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_cell_length_b                   9.4311(15)
_cell_length_c                   10.3177(15)
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_cell_measurement_theta_max      27.49
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_cell_volume                     752.5(2)
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_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_min         2.095
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7316
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_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
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_exptl_crystal_description       plate
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_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     191
_refine_ls_number_reflns         3464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.2457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             3464
_reflns_threshold_expression     'I > 2\s(I)'
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_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              98803
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