Highly selective C–H bond activation of N-arylbenzimidamide and divergent couplings with diazophosphonate compounds: a catalyst-controlled selective synthetic strategy for 3-phosphorylindoles and 4-phosphorylisoquinolines
Yang, Qiaolan; Wu, Chenglin; Zhou, Jianhui; He, Guoxue; Liu, Hong; Zhou, Yu; Organic Chemistry Frontiers 6 (2019) 393–; doi:10.1039/C8QO01148F

data_1554522
_publ_section_title
;
 Highly selective C--H bond activation of N-arylbenzimidamide and
 divergent couplings with diazophosphonate compounds: a
 catalyst-controlled selective synthetic strategy for 3-phosphorylindoles
 and 4-phosphorylisoquinolines
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              393
_journal_paper_doi               10.1039/C8QO01148F
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H20 N O3 P'
_chemical_formula_sum            'C18 H20 N O3 P'
_chemical_formula_weight         329.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_audit_update_record
;
2018-10-15 deposited with the CCDC.
2018-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.969(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6453(19)
_cell_length_b                   11.642(3)
_cell_length_c                   9.808(3)
_cell_measurement_reflns_used    737
_cell_measurement_temperature    173
_cell_measurement_theta_max      19.480
_cell_measurement_theta_min      2.736
_cell_volume                     850.7(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0962
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6393
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.312
_diffrn_reflns_theta_min         1.749
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0762 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.8490. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                2380
_reflns_number_total             3451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01148f2.cif
_cod_data_source_block           mo_20180104-yql-2_0m
_cod_database_code               1554522
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C10(H10), C6(H6), C3(H3), C12(H12), C4(H4), C14(H14),
 C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'