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_1555730
_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         'C12 H14 N2 O'
_chemical_formula_sum            'C12 H14 N2 O'
_chemical_formula_weight         202.25
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 104.569(5)
_cell_angle_gamma                90
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_cell_length_b                   15.085(2)
_cell_length_c                   8.9672(14)
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_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.70
_cell_volume                     1065.7(3)
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_computing_data_collection       'APEX2 (Bruker, 2014)'
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_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
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_diffrn_reflns_limit_l_min       -11
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_diffrn_reflns_theta_full        25.242
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_diffrn_reflns_theta_min         2.701
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
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_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     137
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.2306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0897
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_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2107
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02249_si_002.cif
_cod_data_source_block           d1680_a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1555730
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              45754
_shelx_hkl_checksum              22415