Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization
Shengtao Ding; Ning Jiao; Journal of the American Chemical Society 133 (2011) 12374–12377; doi:10.1021/ja204063z

data_4106558
_publ_section_title
;
 Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed
 Cyanation of Heteroarenes via C-H Functionalization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12374
_journal_page_last               12377
_journal_paper_doi               10.1021/ja204063z
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.3950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3089(3)
_cell_length_b                   14.4090(4)
_cell_length_c                   10.5351(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1401.75(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15911
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.4302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                2101
_reflns_number_total             2460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja204063z_si_002.cif
_cod_data_source_block           z
_cod_database_code               4106558